Today’s best men’s Chelsea boots are the perfect balance of rugged and refined. They create a unique aesthetic that falls somewhere between chic and badass and can look just as good with worn-in men’s jeans as they do with a three-piece suit. Despite the Chelsea boot’s popularity today among men, it has an illustrious past that dates back to 19th century Great Britain.
Once favored by royalty and prized as a useful horse-riding boot, the Chelsea—a pull-on style with elastic panels, or gores, and a back heel tab—has since been transposed into many variations. Dressier versions were popularized in the US in the ’60s with the rise of The Beatles, who frequently wore black leather Chelsea boots with a Cuban block heel (dubbed the Beatle boot). At the same time in Australia, a brand called Blundstone had put a workwear spin on it, creating what would become known as the #500 that’s still one of the best Chelsea boots for men today.
You’ll also find men’s Chelsea boots in a variety of materials, including textured suede and tough, tumbled leather. Dressier Chelsea boots will employ a full leather sole for its cleaner lines whereas others will draw inspiration from the workwear element and use a thick, lugged rubber or crepe sole for added traction and durability.
Whether it’s your first or fifteenth pair, narrowing down the options can be overwhelming. These are Men’s Journal’s favorite pairs of Chelsea boots for men right now based on versatility, longevity, and comfort.
The Best Men’s Chelsea Boots of 2024
Thursday Boot Company Cavalier Men’s Chelsea Boot, $190
Some of the best men’s Chelsea boots come from Thursday Boot Company, a direct-to-consumer brand with some of its top styles available on Amazon. This pair of Spanish-made Cavaliers, a bestseller for Thursday Boot Co., is made from weather-resistant suede and features a leather Goodyear-welted sole and TPU studs for added traction. They’re a safe bet for guys who walk in temperamental weather and play a hybrid role between casual and something a little fancier. The dark brown suede colorway is handsome, but you can’t go wrong with any of the other five leather and suede options.
Ariat’s Booker Ultra Western boot is what you get when you mix the British-born Chelsea boot with old West America. It’s a low-profile, square-toed boot that’s equal parts Chelsea, cowboy, and work boot and is best worn with a dynamite Western shirt. It’s made from hardy leather and is short enough that it doesn’t obscure the taper of your jeans, which is a pain point for some cowboy boot lovers. Ariat’s bestselling Chelsea boots can be “worn all day and after many miles are still comfortable,” one shopper said.
Bruno Marc Suede Chelsea Ankle Boots, $37 (was $55)
Bruno Marc shoes are tremendously affordable and an Amazon staple. The brand’s men’s Chelsea boot is Amazon’s No. 1 bestseller in its category and boasts over 8,300 five-star ratings with a 4.5-star average overall. They might not be made in Italy from the finest materials, but they’re a prime Chelsea boot for men who are new to wearing the style and aren’t ready to pull the trigger on something more expensive. Find this one in eight different colors, including black and brown leather and navy and gray suede.
The Rhodes Blake Chelsea boot draws inspiration from the workwear style of the ’60s. Designed by Huckberry, it perfectly encapsulates the balance of rugged and coolness that many denim-clad, flannel-donning dudes strive for right now. It’s made in Leon, Mexico with leather from a local tannery and has a lightweight, textured polyurethane wedge sole that provides comfort, cushion, and traction. At less than $200, this is an incredible value.
There’s so much to like about Thursday Boot Company, a brand that’s stormed onto the boot scene and has set up shop at the intersection of quality and affordability. Its Legend Chelsea boot is one of those things, with one of the best lug soles you can find on a fashion boot. It comes in a handful of colors, but the black matte and the shade Tobacco, seen here, are by far the most attractive. The matte finish provides a bold but understated look with its lack of sheen and deep chocolate brown hue. It’s the kind of boot that’s best worn with a classic leather moto jacket.
Astorflex’s Bitflex Chelsea boot is made by a sixth-generation family business in Northern Italy that uses fine Euopean-sourced leathers. It features a natural crepe sole, the kind popularized by the Clarks desert boot, and boils over into smart casual style territory with its refined edges. It comes in five handsome shades of brown, but we love the Tobacco suede colorway. A light-colored Chelsea boot like this always looks great with either light or dark-wash jeans. Finish the look with a wool coat or a classic denim trucker jacket.
This is the modern version of the men’s Chelsea work boot from the ’60s that started a wild footwear revolution. The Blundstone #500 Chelsea boot is an Australian icon. It was originally designed as a field shoe for farmers, a work boot for builders, and a problem-solver for workers who needed extra-durable footwear. Today, the #500, along with every Blundstone style inspired by it, suits the same crowd as well as the fashion-forward. It’s one of the “it” boots of the past few years and won’t be off the radar any time soon.
Ace Marks offers a chance to have designer-quality Italian-made footwear at affordable prices by cutting out the middle-man. This Chelsea boot, in the color they call “Diablo Antique,” exudes royalty. It’s instantly eye-catching with its burnished red hue and slim silhouette fit for a king or just a dapper gentleman. Each pair comes straight from Italy made specifically for you.
Amberjack Chelsea Boot, $195
Amberjack is a newer brand, but its Chelsea boots were meticulously designed. These boots are lightweight and absurdly comfortable right out of the box—no break-in time required. The brand wanted to create something that would blend sneaker-like comfort with the durability of a boot and did so successfully. This is a pair that I own and love. It has a generously wide footbed, a thick, city-ready sole, and a subdued hue because of the matte suede. I find it’s best to store them in the bag that comes in the box because the suede is a magnet for dust.
With clear parallels to the Blundstone #500, the Keen Revel IV is ready to take a hit. Made with full-grain waterproof leather, a thick, multi-directional lug sole, and Keen’s iconic toe bumper, this is the Chelsea boot for men who know they’re about to get roughed up by the elements and need some extra protection. Interestingly, the Revel IV is also quite warm, with a rating of -25 degrees. Keen promotes this as snow-ready, which isn’t normal for an open-top Chelsea boot, but many REI customer reviews say they use this as an all-weather boot, including in snow.
Florsheim Foundry Plain Toe Gore Boots, $150 (was $280)
Florsheim has been in business for over 130 years and has made shoes during nearly every modern footwear trend the US has seen. Its Foundry Plain Toe Gore Boot is a take on the men’s Chelsea boot that uses some of the best American leather—Horween Chromexcel. The tanning process for this leather produces an ultra-soft, visually appealing product that looks better the more you wear it.
A very close version of the ’60s Beatle boot, Saint Laurent’s Wyatt Chelsea boot has been a favorite among the ultra-chic. It’s a textbook example of a sharp-toed, slim silhouette boot that pairs masterfully with a slim-fit suit or narrow trousers. It’s made in Italy with very soft, flexible leather and comes with a price tag to prove it. But if you’ve been looking for the best dressy Chelsea boot, this is the one. It’s also available in a very nice-looking black and tan suede.
Men’s Journal aims to feature only the best products and services. If you buy something via one of our links, we may earn a commission.
When temperatures drop, it’s time to upgrade your winter boots. When considering a new pair, evaluate your specific needs and the climate where you reside. Are you dealing with heavy snowfall or a drier winter? Do you spend a significant amount of time outdoors, or do you prefer the convenience of slip-on boots for commuting? Perhaps you’re in search of a dressier option for upcoming formal events, or maybe you need a seriously insulated boot to combat the cold.
Perhaps, like me, you require more than one style. Winter boots offer a myriad of options to choose from, so to help streamline your decision-making, we’ve curated a selection of the best men’s winter boots for various needs. However, if we had to pick one favorite, our best overall boot is the winterized L.L.Bean 10″ Maine Hunting Shoes with Gore-Tex and Thinsulate.
Why You Should Trust Me
In addition to writing for Men’s Journal, I have covered menswear, fragrances, watches, grooming, and style for Inside Hook, Robb Report, Esquire, and Men’s Health. I served as the market editor at Esquire for several years, scouring the industry for the best garments and goods that were not only worth the investment but also made for compelling stories and good advice for our readers.
I have always tried to add a timeless element to whatever I write. Although trends are interesting and relevant, my heart has always been drawn to more perennial guidance and themes. My obsessive-compulsive tendencies are both a blessing and a curse and while I often delve into researching items to the point of exhaustion, it’s this approach that often positions me as a go-to person for advice. Whether it’s about coats, colognes, or turntable needles, people recognize that I’ve done the legwork. I enjoy inspiring others around me to seek out their unique interests in things that might make their life better.
What to Look For in a Pair of Winter Boots
Traction: Regardless of conditions, prioritize a sole with excellent traction. While I usually lean toward the timeless appeal of leather soles, the winter season warrants a shift toward the practicality of rubber soles. When it comes to boots designed for snow or hiking, seek larger, more robust treads. For lifestyle boots, look for Vibram or chunkier lug soles, which can blend with a formal aesthetic but still provide traction for slippery slopes. Rubber soles include varieties like PVC, which is renowned for its water-resistant properties, and rubberized polyurethane, which boasts durability, flexibility, and are lightweight. While there are many different, proprietary sole materials and styles, the key is making sure the treads are sturdy, deep, and grippy.
Insulation: All winter boots should provide a significant level of warmth. Some styles incorporate insulation such as Thinsulate or a removable inner layer, while others use proprietary materials. High-quality insulation effectively traps air, is lightweight, and prevents the loss of radiant heat from your feet and soles. Natural textiles such as shearling and wool are also excellent choices for keeping your feet dry and warm, thanks to their natural heat-trapping and breathable properties. Unlined leather in more lifestyle or dress boots may not offer the same level of insulation, however wearing thicker thermal or merino wool blend socks will help keep your feet snug and dry.
Waterproofness: Given that you are likely to experience anything from snow and slush to rain, a good winter boot should provide a degree of water protection. All-rubber boots offer maximum waterproofing, while two-piece boots, such as leather and rubber combinations, can provide waterproofing with more breathability. One-piece leather boots will also be effective; the higher the tongue and overall height of the boot, the drier your feet will likely be. Fully waterproof boots tend to sacrifice a bit of breathability for maximum protection while water-resistant boots allow your feet to breathe more and often provide greater flexibility.
Brand Quality: Even if not exclusively focused on footwear, these brands exhibit a meticulous commitment to both the construction and the incorporation of technologies that contribute to making a quality winter boot. Many of the recommendations below feature tried and true styles that men consistently turn to every winter. These boots have repeatedly proven their reliability in challenging conditions, earning them a well-deserved reputation for consistency.
Best All-Around Winter Boots: L.L.Bean Maine Hunting Shoes, 10″ Gore-Tex/Thinsulate
L.L.Bean Maine Hunting Shoes
Courtesy Image
I always keep a pair of these boots ready for inclement weather, as they’ve proven to be my go-to for navigating through the slushy streets of NYC while keeping my feet completely dry. Whether it’s shoveling snow from the driveway, commuting to work, or spending time with friends on a snowy day, these Maine Hunting Shoes effortlessly handle it all. This upgraded version of the classic duck boot (or hunting shoes as L.L.Bean calls them) is specifically designed for cold weather, featuring a waterproof Gore-Tex liner and Thinsulate insulation.
Best Winter Boots Value: Columbia Bugaboot III
Columbia Bugaboot III Boots
Courtesy Image
The renowned Columba Bugaboot is consistently mentioned as one of the best winter boots due to its seamless integration of waterproofing, protection, and warmth. While there may be options that surpass the Bugaboot in terms of technical intricacies, it easily meets all criteria for most people looking for an option designed specifically for cold weather, all at a great value. Featuring waterproof leather, omni-tech waterproof seam-sealed construction, 200g insulation, a TechLite lightweight midsole for comfort, and an Omni-Grip traction rubber sole, the Bugaboot boasts a myriad of trademarked and researched technical specifications with a proven track record.
Best Winter Hiking Boots: Huckberry x Diemme Roccia Vet
Huckberry x Diemme Roccia Vet Hiking Boot
Courtesy Image
Crafted in collaboration with Diemme, (the storied hiking footwear brand) these rugged, waterproof hikers from Huckberry combine great aesthetics with exceptional functionality. Made in Italy, the waterproof suede uppers are seamlessly joined to a robust rubber mudguard, providing reliable protection against whatever challenges the trail may present. With their full-lined leather upper, highly treaded yet lightweight sole, and ankle support design, these boots offer exceptional comfort—a necessary requirement for all-day hikers.
Best Extreme Cold Winter Boots: North Face Chilkat V 400
North Face Chilkat V 400 Boots
Courtesy Image
When the temperature really drops, the North Face Chilkat rises to the occasion, consistently earning high ratings as one of the warmest winter boots available. Featuring proprietary 400g Heatseeker insulation, a waterproof full-grain and leather suede upper, and a proprietary Surface Control sole, this boot is well-equipped to handle the harshest winter conditions. This updated version is now slightly lighter, while still maintaining its durability. Although many highly technical winter boots may sacrifice aesthetics, the Chilkat with its tri-tone brown, black, and hunter green, offers a stylish option for those seeking serious winter protection.
Best Snow Boots: Sorel Caribou
Sorel Caribou Boots
Courtesy Image
Much like the Bean boot, the Sorel Caribou has solidified its position as an icon in the world of winter footwear. When temperatures drop and snow accumulates, these robust boots are my go-to for trudging through deep banks. Renowned for their exceptional comfort, the Caribou boots also feature seam-sealed waterproof construction and a lug sole design, ensuring superior traction in snow. Moreover, these boots are warm as heck, thanks to a removable and washable felt inner and sherpa lining at the cuff. And, despite their tank-like durability, style is not compromised.
Best Waterproof Winter Boots: Hunter Original Insulated Short Rain Boots
Hunter Original Insulated Short Rain Boots
Courtesy Image
The is synonymous with rain, and for good reason: They excel at keeping your feet dry! This insulated version of their popular short boot is specifically designed for colder weather, ensuring your feet stay warm even in temperatures as low as 23 degrees. Crafted from all-natural rubber, each boot undergoes vulcanization for superior waterproofing while the treaded sole provides excellent traction, keeping your feet firmly planted wherever sleet may fall.
The renowned Columba Bugaboot is consistently mentioned as one of the best winter boots due to its seamless integration of waterproofing, protection, and warmth. While there may be options that surpass the Bugaboot in terms of technical intricacies, it easily meets all criteria for most people looking for an option designed specifically for cold weather, all at a great value. Featuring waterproof leather, omni-tech waterproof seam-sealed construction, 200g insulation, a TechLite lightweight midsole for comfort, and an Omni-Grip traction rubber sole, the Bugaboot boasts a myriad of trademarked and researched technical specifications with a proven track record.
Best Dress Winter Boots: Thursday Boot Co. Captain Storm King
Thursday Boot Co. Captain Storm King Boots
Courtesy Image
Thursday Boot Co. is known for their very accessible, no-nonsense, quality boots with timeless aesthetics. The robust and enduring Storm King furthers this reputation with its Goodyear welt construction, fully lined leather interiors, steel shanks, Kevlar laces, and reinforced eyelets, resulting in a remarkably durable pair of boots suitable for both work and weekends. The juxtaposition of the refined upper and the seriously rugged sole makes this an excellent choice for occasions demanding both formal style and resilience in winter weather.
Best Moc Style Winter Boots: Red Wing Storm Welted Classic Moc
Red Wing Storm Welted Classic Moc Boots
Courtesy Image
The is easily recognizable by its stitched, rounded toe and white crepe, rubber wedge sole design. This traction tread sole incorporates a split-toe reverse storm welt for enhanced water resistance. While not explicitly designed for deep snow, the oil and waxed nubuck construction ensures durability and resilience under various conditions, and these boots will gradually mold to your feet over time. This Moc Toe stands as a true lifestyle hard-wearing hybrid adorning outfits on city streets and winter landscapes alike.
Best Slip-On Winter Boots: Blundstone #1944 Chelsea Boot
Blundstone #1944 Chelsea Boots
Courtesy Image
Blundstones have experienced a significant resurgence in recent years, and for good reason. They boast a sleek and minimal slip-on Chelsea style that exemplifies no-fuss form and function. The #1944 model builds upon their classic men’s slip-on design by incorporating enhanced features such as water-resistant leather, a robust TBU-treaded sole, a removable footbed with shock absorption technology, and leather lining. Lightweight, comfortable, and effortlessly easy to slip on and off, these Blundstones are a stylish and practical everyday choice.
Best Alpine Winter Boots: Danner Mountain Light
Danner Mountain Light Boots
Courtesy Image
Crafted in Portland, Oregon, Danner epitomizes quality and heritage in their classic alpine boot. Gore-Tex liners provide maximum waterproofing and breathability, and their trademark Vibram Kletterlift sole is specifically designed to absorb shock and provide traction on both wet and dry surfaces. Quality control is also paramount as the full-grain leather upper goes through six different tests before Danner approves it. And the boot silhouette, lacing structure, and eyelets all just make it darn stylish.
Men’s Journal aims to feature only the best products and services. If you buy something via one of our links, we may earn a commission.
Finding the right gifts for men for the guys in your life can be daunting, especially when they offer guidance like “I don’t need anything.” But Huckberry, a top online stop where guys find the gear they want and discover new, future-favorite brands, makes finding the right gift much easier.
This year, Huckberry has a wide selection of gifts for the rugged man who loves adventure, for the discerning fashionisto, and even for the coffee and whiskey lover. There are plenty of exciting gifts to find for under $50 from brands like Yeti and Zippo, but the brand also offers some of the nicest men’s apparel and footwear, including its famous waxed canvas jacket that was worn by Pedro Pascal in the hit TV series The Last of Us.
The best gifts for men at Huckberry right now are spread across multiple categories and range in price from $7 to $298. Aside from the prized, aforementioned jacket, Men’s Journal anticipates the Solo Stove tabletop fire pit to be a hot gift item, alongside slippers from Greys and classic beanies, which are no-brainer stocking stuffers. Regardless of the type of man you’re shopping for, the brand has something that’ll hit the nail on the head as soon as he opens it. There are the 20 best gifts to buy at Huckberry right now.
Flint and Tinder Flannel-Lined Waxed Trucker Jacket
The Flint and Tinder Flannel-Lined Waxed Trucker Jacket is the No. 1 bestselling item at Huckberry and the ultimate gift for the rugged man. It’s on the pricier side, but it’s the one that’ll have him telling stories about how excited he was after opening it up for years to come. It’s durable, water-resistant, and only gets better with age as it develops a beautiful patina.
Solo Stove made fire pits even cooler than they already were—and portable. The easy-to-use Mesa XL Tabletop Firepit packs all the Solo Stove punch into a compact size that’s perfect for apartment balconies, side decks, and terraces. It comes in three attractive colors and burns wood or pellets.
Slippers are a traditional gift for men that need replacing about once a year (or every other) depending on how much they get used. Greys offers something a little more with its slippers. Made in Portugal, these slippers are crafted from wool, which is naturally odor-resistant, moisture-wicking, temperature-regulating, and breathable. All of this on top of a grippy rubber sole is enough to be a perfect holiday gift.
Most men love bacon, which is why these Archie McPhee Bacon Candy Canes make for an equally hilarious and delicious stocking stuffer. Eating them traditionally is fine, but the brand also recommends trying them crushed up and baked into some chocolate peppermint bark—that’s a big ol’ “yes” from us.
Whiskey gifts often get overplayed and without much thought, but Whiskey Peaks offers something unique with this decanter and glasses set. From its collection of barware that features the topography of the world’s most famous mountains, this set sees Washington’s Mt. Rainier, the highest volcanic peak in the lower 48, at the bottom of each of the three glass pieces. If he’s more into beer, there’s also a beer stein version.
Another Huckberry classic, the 10-Year Pullover Hoodie has over 400 reviews attesting to the quality and longevity spoken of in its name. Described by the brand as “beefy,” this thicker hoodie is “best for cold weather season,” as stated by one shopper. Many also say they run a size small, so consider that when shopping.
The No. 2 bestseller at Huckberry is the 365 Pant. Available in four fits ranging from slim to relaxed, the 365 pants will be that multiple-times-per-week staple that he can rely on to always look great. Falling somewhere between a pair of jeans and a chino, shoppers who’ve left reviews agree that they’re one of the most comfortable pants a man could have.
This is a sure bet for the Zippo-collecting giftee. It’s also a great idea for anybody who enjoys candles or interesting everyday carry items. This Zippo depicts Norman Rockwell’s “Man’s First Step on the Moon,” which was by far the coolest-looking model in a series of the brand’s art-inspired lighters.
A nice pair of leather boots, like the Tyler Chukka from Rhodes, is a gift that will last for years. Made in Leon, Mexico, this chukka boot in the Hickory colorway is exceptionally versatile and even works great as an office shoe. If he’s a city commuter, he’ll love these.
He may already own a Yeti or Hydro Flask water bottle, but if he’s a hot coffee drinker, this mug will help keep it hot for far longer than a standard mug. Stackable for easy storage, Yeti’s 14-ounce rambler mug comes in navy, gray, and white.
A very Ron Swanson gift, the Outdoor Fellow Woods-scented candle is a no-frills way to perk up any room in the house. The No. 14 candle is available in several other scents, including Ash Spice and Coastal Forest.
Rototo’s Old School Crew Socks are a step back in time to when skateboards looked like fish and basketball shoes had no arch support. They’re as well suited for a pair of his favorite boots as they are his favorite pair of Vans sneakers, so pick his favorite color among four colors for an easy accessory gift.
AirTags are going to be one of the top gifts this holiday season which means dressing them up with cool accessories, like Atech Innovations Multi-Tool, is a must. This doodad functions as a hex wrench, bottle opener, nail puller, and box opener, which is especially convenient for opening gifts.
Another top seller at Huckberry, the Relwen Windzip Jacket is an everyday, all-the-time jacket that’s perfect for chilly days inside working from home, running quick errands, or layering when heading out for the night. It’s flush with features, like water resistance and tons of pockets, and comes in four neutral colors.
If you’re the sweater-giving kind of person, the Wellen Recycled Cotton Headlands Sweater is a fantastic gift for any man. It’s made from recycled cotton, acrylic, and polyester that are woven together to make a unique-looking garment at an excellent value.
Like slippers, hiking boots have to be replaced every so often, and that makes them a meaningful gift. These Vasque Skywalk hiking boots feature a Gore-Tex membrane that keeps water out and an abrasion-resistant upper made from mesh and leather that looks nice and wears tough.
The Barebones Stainless Steel Scrubber is a dream come true for cast iron skillet users. The chain coating helps scrape the crust from burgers and tomahawk steaks past to get your pan back to square one for the next dish.
Hailing from Ventura, California, Sundream’s dark roast coffee features fruity, nutty, and chocolatey notes that will invigorate the nostrils. There are also tasty light and medium roasts available from the family-owned, artisanal coffee brand.
Beanies are such an easy gift for men, and Huckberry’s take is one to note. Made in Japan by a manufacturer that specializes in beanies, this one uses a blend of acrylic, wool, nylon, and spandex to form a must-have winter essential. Grab one for him (and maybe yourself) in one of 10 colors.
A layer that truly oozes the Western wear aesthetic, Flint and Tinder’s Flannel-Lined Quilted Waxed Rancher was designed to be tough like the men who wear it. With a thick 10-ounce waxed canvas shell, four ounces of additional insulation, and a flannel lining to top it off, this is the jacket that’ll help him work outside even when the plains are frozen over. For all others who don’t tend cattle, it’s a solid option for winter, especially with a 10-Year Hoodie or a nice flannel layered underneath.
Men’s Journal aims to feature only the best products and services. If you buy something via one of our links, we may earn a commission.
Despite the popularity of trail runners, sandals, and hiking sneakers, there’s still plenty of value in a pair of classic hiking boots. The added durability, traction, and ankle support of hiking boots make them the preferred option for longer hikes and navigating tricky terrain. Keen is one of the leading hiking boot brands, and some of their best shoes are discounted on Amazon right now.
Keen’s Targhee III hiking boots are available on Amazon for as little as $85, an $80 savings on the $165 shoes. Savings vary by color and size, with discounts that range from 30% to 49% off. Made from a leather and mesh upper with a grippy rubber sole, the boots feature a mid-ankle cut and a breathable waterproof membrane that allows for airflow while blocking moisture.
KEEN Men’s Targhee III Mid Height Waterproof Hiking Boot, from $85 (was $165) at Amazon
The third iteration of the Targhee boot is designed to be a slightly leaner version of the Targhee II, while retaining the earlier model’s waterproof leather upper and grippy rubber sole. Keen’s Targhee boots are designed for day hikes, as opposed to backpacking or highly technical trails, so they’re a good option for the everyday hiker who prefers a boot to a sneaker.
“I purchased these for a trip to the Acadian salt marshes in Nova Scotia,” one five-star reviewer said. “They were (are) perfect! They feel really good. I bought a wide size and they are just perfect. My toes feel so good. Plus, they lace up tight and snugly where it counts. No shucking and sliding… no blisters or rubbing. Perfect!”
Keen’s outdoor bona fides belie the fact that the brand’s history is fairly recent. The brand was founded in 2003 — making it significantly younger than peers like Salomon, Merrell, and Danner — but Keen’s impressively comfortable and affordable footwear has given the brand a firm foothold (pun intended) in the hiking shoe market.
The brand’s commitment to eco-friendly production has also endeared it to outdoorsy types. The Targhee boots are made with Leather Working Group-certified leather, meaning the leather is produced with mindful water and energy usage. The water-repellent material is PFAS-free.
These have over 4,200 five-star ratings on Amazon, and a common theme in the reviews is comfort. Several wearers noted that there was “no break-in period” or that the break-in period was “very easy.” The wide toe box was a selling point for many reviewers, who appreciated the wiggle room and lack of pinching.
If you’re looking for a pair of comfortable boots for wet winter hikes, Keen’s ankle-cut waterproof Targhee III boots are a great option, but you’ll want to act fast to take advantage of this deal of up to 49% off while it lasts.
Men’s Journal aims to feature only the best products and services. We update when possible, but deals expire and prices can change. If you buy something via one of our links, we may earn a commission. Questions? Reach us at shop@mensjournal.com.
Moc toe boots have been essential equipment for sportsmen, tradesmen, loggers, and factory workers since the 1950s. Then, somewhere along the line, these heritage boots also became prized purely for their rugged aesthetics. They’re named for the Native American moccasins that inspired their style of construction, and recognizable by their separate U-shaped piece of leather on the top that is sewn to the walls of the toe.
While the design is ancient, Red Wing was the first company to create a moc toe boot, in 1952. The original version had a rubber sole that made them particularly useful for sportsmen, and the moccasin design left more room for toe movement while the stitching made them more flexible for walking. The higher toe walls also made them more protective than traditional boots, so they soon became popular with factory workers who preferred to keep all of their toes. Not coincidently, the was the overall best moc toe boot out of our test—because they’re the perfect combination of value, heritage, and versatility.
Why Should You Have a Pair of Moc Toe Boots?
Originating in the timberlands of Minnesota, moc toe boots are a uniquely American invention born out of the necessities of American industry and terrain. Borrowing in their construction something tried and true for Native Americans for thousands of years, they’re rugged, sporting, and suitable for everything from hunting to welding to barhopping. Every man needs a pair of moc toe boots in his closet.
What are Moc Toe Boots Good For?
Depending on the design and construction, moc toe boots can be rugged enough for hunting, or factory work and construction (with reinforced toes for added protection). Some use modern materials to be ultra-light and as comfortable as a sneaker, while others are made of the finest leathers in the world and are better suited for wearing with a sport coat. When choosing a moc toe boot, you should decide first if it’s for function, fashion, or a mix of both.
Rugged options can require much more break-in before they’re comfortable, but will hold up to serious abuse for years to come. If you don’t need that kind of durability, you may want an option that will be instantly comfortable without any break-in period. Work-focused moc toe boots can be quite heavy, while others are designed for nimble hiking and travel that doesn’t involve chopping down trees.
Many are even recraftable, meaning that they can be fixed up to look near-new after many years of use. There are weatherproof options, value options, and hand-made investment-grade boots that will require some care but will last you a lifetime. In short, there’s a moc toe boot for everyone.
How We Tested Them
I started with the best moc toe boots available, and then narrowed them down even further to the ones that would cover the greatest range of wearers, uses, and budgets. Then I tested them all out. I took one pair across Scotland. Another pair joined me on a Montana dude ranch. Breaking them in, walking and hiking in them, obsessing over their details, and talking to some of the people who produce them were all part of the process.
I’ve been covering gear and style from a home base in Los Angeles and now Charleston since 2006, for outlets including The Wall Street Journal, Wired, Maxim, Gear Patrol, Fatherly, and Men’s Journal. Whether it’s testing out gear, bags, clothing, and accessories on my own adventures, or profiling designers and craftspeople who make them, it’s been one continuous process of discovery, and an ongoing search for the essentials that bring joy, serve a purpose, and add value to our experiences.
Boots are my most beloved and obsessed over clothing item of all. They’re not just footwear, functionality, or fashion, but a combination of all three that also makes a statement of intent. They tell strangers how hard you work—or play. They can convey your sense of style, your attitude, and even your priorities. I can look back and remember big trips I’ve taken and entire phases of my life based on the boots I was wearing at the time.
Over the course of my continued education about the materials and craft that make for truly great boots, I’ve visited tanneries, met cutters and sewers on factory floors, and been schooled by second and third-generation shoe makers on the ins and outs of Goodyear welts and gusset tongues, of lug soles and wedges, of heel stacks and steel shanks. What we love the most, we learn about with both joy and a purpose to share that knowledge.
Best Overall Boot: The Red Wing Heritage Classic Moc
While other boots on the list surpass it in comfort, style, and features, the Red Wing Heritage Classic Moc is the perfect combination of value, heritage, and versatility. Therefore, it’s the boot with which most people should begin their search. We tested it out in the new Alpine Portage color—a warm grey that works well with any jeans or trousers.
They have recraftable rubber soles, the interior is unlined and decidedly utilitarian, and they have a gusseted tongue—meaning a tongue sewn to the sides of the upper to prevent water or dirt from getting in. The leather is durable, but also very rigid on first wear, so these will take some serious breaking in. They’re rugged enough for manual labor or hunting, but in terms of style, they could also be worn with a nice pair of jeans, to work in an office, or even out to dinner.
Because the toe isn’t made of two separate pieces of leather, the Alden 403 isn’t technically a true moc toe—but it’s certainly the most iconic. Beloved film character Indiana Jones famously wore these because actor Harrison Ford loved them so much that he nixed the script-suggested Red Wings and insisted on the Aldens.
The 403 is the same style as Indy’s boot, but uses a dark brown Horween Chromexcel leather. We found the 403 to be instantly comfortable with zero break-in needed—more comfortable on the first wear than every other boot on the list. They do fit wide, so Alden suggests ordering a half-size down. They don’t have a gusseted tongue, so there’s not as much protection from the elements. But for the price, they’re unlikely to be your go-to boots for getting dirty.
They are the most expensive boots on the list at $655, but through our conversations with both Alden and Horween, it’s clear that they’re still not overpriced considering the workmanship and materials that go into them. It’s worth signing up for notices on theshoemart.com for a chance to score factory rejects at a solid discount. Seconds inventory is limited, so you’d have to luck out on sizing.
is based in Spokane, WA—the heart of logging country, where they’ve been making boots since the 1960s. They’re the most durable handmade moc toe boots you can buy. With thick leather, a beefy heel stack, lug sole with steel screws, and serious stitching, they’re an extremely heavy duty work boot made with an incredible attention to detail. Included in the box is a carbon slip from the factory floor, where every step of the process is signed by the craftsperson who handled it.
Nick’s Boots owner, Shuyler Mowe, says that they sell “a ton of these as work boots to tradespeople and those who appreciate that chunkier aesthetic.” They are heavy and need some serious breaking in, but these are lifetime boots. The toe box is pretty rigid out of the box, so order a wider size if there’s any concern for width. They have a gusseted tongue, and they also come with false tongues, which are additional pieces of leather that help prevent any pinching from the laces. The soles, with their gleaming steel screwheads in the treads, are a standout detail. They have quick ship options, but if you have time to wait, they can be fully made-to-order, customized by color, sole type, height, and more.
Pros
Cons
👍 Handmade
👎 Heavy
👍 Made-to-order and quick-ship options
👎 Require breaking in
👍 Recraftable
👎 Longer wait for made-to-order
[$580;]
Rancourt Harrison Redux
Stinson Carter
Best Boots for Travel: Rancourt Harrison Redux
After testing these on a trip to Scotland, we can say that as an everyday (and night) travel boot, Rancourt’s Harrison boots strike the perfect balance between durability, comfort, and dress code versatility. They’re handmade in Maine out of Horween Chromexcel leather, which naturally has some water resistance and will develop an aesthetically pleasing patina over time. They don’t need much breaking in and the rubber sole is soft enough to stand on for hours. You can wear them tromping across the cobblestones of Edinburgh with a backpack or out to dinner with a sportscoat.
Another bonus is that they’re flexible enough to drive in comfortably over long distances, unlike the Harrison’s rugged competitors. It’s a camp moc style of boot, meaning it bears more moccasin DNA than any other boot on the list. With more stitching comes more chance for the threads to fray over time, but Rancourt can resole or restitch your boots if needed.
Danner’s new is a modern interpretation of a moc toe boot, optimized for lightness, comfort, and all-weather/terrain use. Not only are they lightweight, they’re waterproof and breathable, thanks to the Gore-Tex lining and durable nubuck leather. Because they have the multi-layer cushioning of a sneaker—including a removable OrthoLite footbed, a Vibram midsole, and a Vibram outsole—these boots are perfect for hiking or travel. But unlike a sneaker, they can be resoled after years of wear-and-tear through Danner’s Recrafting Center.
While Danner says they run true to size, we found them to be slightly on the narrow side—and as of now, they don’t come in wide sizes. But if comfort for hiking or travel to more casual destinations is your priority, these are hard to beat for the price and features. In short, for moc toe looks with a trail sneaker feel, these are the ones for you.
Pros
Cons
👍 Weatherproof
👎 Casual style is less versatile
👍 Comfortable straight out of the box
👎 No wide sizes
👍 Lightweight
👍 Recraftable
[$240;]
Grant Stone Brass
Stinson Carter
Best Dressy Boot: Grant Stone Brass
Made of Horween Chromexcel leather, the black version of Grant Stone’s Brass boot are bestsellers for the company. In this rich black, they are a perfect choice for anyone who wants to dress up their moc toe, whether for the office or out on the town. That said, there are a dozen different colors of the Brass boot—and it can also be also ordered with a wedge sole—so there’s a style to fit anyone’s mood, taste, or use case.
Grant Stone CEO Wyatt Gilmore has boot pedigree in his blood: his grandfather worked at Alden for 60 years and his father worked there for 15 years. The attention to detail is evident in the meticulous hand sewing of the moc toe itself, which Gilmore says is difficult to produce because only the best craftspeople are skilled enough to do the prominent hand sewing required. We found them to be comfortable without a break-in period, though they are on the heavier side. Grant Stone is known to carry a wide range of sizes and widths in stock for most of their boots, so even if you have an odd size, chances are they’ve got it ready to ship.
At just under $200, the Thursday Boot Co. Diplomat boots offer a lot for the price. They look great and don’t feel the least bit budget-minded in construction. They have a Vibram wedge outsole, a steel shank for stability, corkbed midsoles for comfort that adapts to your foot over time, antimicrobial insoles, and the laces are Kevlar-infused for durability. They are lined with glove leather, and they’re built on a Goodyear welt sole, so they can be resoled. Thursday says that they’re handmade in small batches, though the hand-finishes are not as apparent here as they are on the likes of Alden and Nick’s—nor would we expect it for the price.
While the leather isn’t as nice as some options on this list, these boots punch above their weight in every category. We found them to be comfortable without much break-in, and they fit true to size. They don’t show up with a fancy box, felt shoe bags, and extra laces, but they deliver on the features that are important. They would be a great entry-level Goodyear welt boot to begin a collection, or to add to your stable as knock-around boots.
The Allen Edmonds Carter weatherproof boots were a favorite from testing. They’re extremely comfortable with zero breaking in, and despite the commando soles, they’re also surprisingly light. The Horween Chromexcel leather will only get better with age and feels as good to touch as it does on your feet. The leather lining is supple, and the padding on the tongue and insole are surprisingly plush.
Weather-wise, these could go on in early fall and stay on until spring. Style-wise, they’re just as versatile. You could travel with them, commute with them, or wear them with a suit. Aesthetically, the Carter strikes the balance between dressy and rugged better than any other boot we tested. They fit true to size, and while they’re pricey, they do go on sale for significantly less than MSRP. The same cannot be said for the other top-tier moc toe boots on this list.
You probably know Lucchese for their cowboy boots, and they do make some of the best. As such, their Ranger II boots bring a Western vibe to the moc toe boot. Handmade like Lucchese’s cowboy boots and ropers, the Ranger II combines the moc-toe style with a beefy rubber sole offering excellent traction and cushion, and the tread is spaced to not hold on to mud and muck. Testing these out on a ranch in Montana was no problem. The soles gripped the terrain like hiking boots, and you could still wear these to dinner or a honky-tonk with a nice pair of pants and a button-down.
The suede upper on the version we tested looks rugged but is deceptively soft, so no breaking in was needed. The glove leather lining is smooth as butter—no other boot lining comes close to its suppleness. An amply padded interior and velvety glove-leather lining make these the most instantly comfortable moc toe boots we tested.
Overland Knocks It Out Of The Park As Usual With These Waterproof Leather Boots
Men’s Journal aims to feature only the best products and services. We update when possible, but deals expire and prices can change. If you buy something via one of our links, we may earn a commission. Questions? Reach us at shop@mensjournal.com.
When it comes to footwear, we tend to lean towards boots ourselves. They just have a style to them that can’t be beaten. Also, in our eyes, they can go with pretty much any outfit you got. Go to work or to the bar with boots on and you’ll be good to go. Such is the case with the Jakob Shearling-Lined Waterproof Leather Boots from Overland.
Overland is a brand we’ve written about before and one we will continue to write about in the future. That’s because when it comes to leather goods, you can’t go wrong with their product. Top-of-the-line leather crafted to make fashion that elevates any guy’s wardrobe. One of their best being the Jakob Shearling-Lined Waterproof Leather Boots.
Overland
Look at the Jakob Shearling-Lined Waterproof Leather Boots. They’re a great pair of boots just on a visual level. That sleek, simple design gives them a versatility that can’t be beat. And there’s that hint of the shearling lining inside that peeks out a bit that gives them a little more of a visual oomph.
That lining doesn’t just add to the style. Nor does the leather. All of those elements combine to make a pair of footwear that looks good but feels even better. It’s well-insulated to keep you warm and it’s waterproof so you don’t gotta worry about rainstorms soaking you to the bone. With comfortable insoles preventing your feet from feeling beat up all day long, these are a perfect pair of boots in our eyes.
Overland hasn’t let us down before and they haven’t done it now. The Jakob Shearling-Lined Waterproof Leather Boots are the kind of footwear that every guy should have in their collection. When the weather is too brutal for a regular pair of boots, go with these. You’ll look as good as you feel when you got these on.
The next time you step out, you should be wearing Chelsea boots. Yes, Chelsea boots. You’ve seen them on the likes of The Beatles, Ryan Gosling, and Ryan Reynolds (to name just a few famous examples), and if you don’t have a pair, now’s the time to get hip to your new favorite boot. They’re both on-trend and yet utterly timeless, with a history that stretches back to Great Britain in the 1800s.
Once favored by royalty and prized as a useful horse-riding boot, the Chelsea boot style—a pull-on boot with elastic sides, or gores, and typically a back heel tab—has taken on a number of variations over the years. Yes, The Beatles wore black leather Chelsea boots with slim tailored trousers, and you can wear yours in much the same way—if they happen to be made from sleek, shiny leather. Chelsea boots are the perfect balance of rugged and refined; they’re ever-so-slightly edgy and seriously cool.
Chelseas also come in materials like textured suede (useful for wearing with jeans) or more rough, tumbled leather (again, great with jeans or garment-dyed chinos). You can wear them in the summer months—they’re less stuffy than thick winter boots—yet they’re also easy to style in the fall and winter. With so many varieties available, you can pick up one pair that strikes the right balance between dressy and casual, or get multiple sets to suit different occasions. Whatever your strategy, these are our favorite Chelsea boots of 2022.
The Best Chelsea Boots of 2022
For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!
Which men’s shoes have stood the test of time? Trends come and go, but there are a handful of stalwart styles that won’t be disappearing anytime soon. Some, like the Oxford, are turn-of-the-century relics that have been cemented into the formal footwear canon. Others, like Adidas Stan Smiths, have a vintage appeal that gets even better with age.
Rather than chasing fads, it’s important to have a few pairs of versatile men’s shoes in your closet that you can wear—and look good in—for years to come. We spoke to New York-based fashion stylist Seppe Tirabassi and got his picks for the essential shoes every man should own, plus his advice on when to wear them and how to pair them.
Essential Men’s Shoes Every Guy Should Own
Sebago Classic Dan LoaferCourtesy Image
1. The Penny Loafer
“A loafer is a must-have for any guy because it works double-time as both a dressy shoe and a casual shoe,” Tirabassi tells Men’s Journal. “When you don’t feel like adulting and tying your laces, you can slide into a loafer after throwing on a pair of ripped jeans and a T-shirt. It’s an effortless way to elevate your look. And of course, wearing loafers with a suit is perfectly acceptable for any formal dress code, except for black or white tie.”
Our Picks:
Clarks Desert BootCourtesy Image
2. The Chukka (a.k.a. the Desert Boot)
The chukka is a classic men’s ankle boot, and it’s a great pick for cooler weather in the fall through the spring. Chukkas generally have uppers made from leather or suede that’ll soften and mold to your foot over time, and Clarks Desert Boots have the added bonus of a bouncy rubber crepe sole.
“For me, the perfect moment for wearing a chukka is when you’re grabbing a coffee and going for a nice Sunday stroll in the park,” Tirabassi says.
Our Picks:
Polo Ralph Lauren Bryson Leather Chelsea BootCourtesy Image
3. The Chelsea Boot
“Few boots are as versatile and timeless as a Chelsea boot,” says Tirabassi. “They go with pretty much anything that’s in your closet from the fall through the winter and the spring.”
Chelsea boots are made with all kinds of leather and suede (even exotic ostrich leather), and you’ll find them in a range of colors.
“The streamlined shape of a Chelsea instantly elevates an outfit without looking like you’re trying too hard,” Tirabassi says. “And because they have elastic sides instead of laces, they’re easy to slip on and really comfortable.”
Our Picks:
Cole Haan Modern Classics Wingtip OxfordCourtesy Image
4. The Oxford
“Just like every man needs an expertly tailored suit stashed in his closet, he also needs a solid Oxford shoe to go with it,” Tirabassi says.
No matter what kind of formal occasion you have on the calendar, an Oxford shoe is a solid footwear choice. Tirabassi advises shelling out for a quality pair—these shoes are reserved for special moments, after all, so they should look (and feel) good. Better yet, if you take good care of them, one pair of Oxfords could easily last a lifetime.
“Wish I could say the same thing about a suit,” says Tirabassi. “Waistlines change as you age, but your shoe size? Not so much.”
Our Picks:
Birkenstock Arizona SandalsCourtesy Image
5. Birkenstock Arizona Sandals
Birkenstock Arizonas are unusually versatile for a pair of sandals. First, they come in a wide range of colors and materials to match any wardrobe or style preference. Second, you can wear them to the beach, around town, and even with a pair of thick wool socks (something that would be a cardinal fashion sin with other sandals). But their best quality might be how easy they are to wear.
“Ever since I started wearing Birkenstocks as a kid, I still haven’t found a pair of sandals more comfortable than these,” says Tirabassi. “I’ve never not had a pair or two in my closet.”
“Everyone needs a simple white sneaker on their shoe rack, and this is the one to get because it’s both timeless and retro-feeling at the same time,” says Tirabassi. “You can wear them with literally anything, from shorts to jeans—even a suit if you want to make a statement.”
The decades-old model now comes in a wide range of colorways, but it’s a good idea to start with a classic white pair. (Check out our white sneakers guide for other stylish options.)
“There’s something to be said about footwear that you can throw on quickly when you’re running late,” Tirabassi says, “and I always keep a pair of Vans by the door for that reason.”
He’s worn Vans Checkerboard Slip-Ons since elementary school, and they’ve served him well as inexpensive men’s shoes for everyday wear. If you’re not into the checkerboard pattern, Vans has many solid-color options as well.
“I grew up in Maine, and I can’t remember a winter spent without these boots,” Tirabassi says. “They’ll keep your toes dry and warm in the rain, slush, or snow, and they’re very comfortable with a pair of thick socks.”
They’ve become a style icon, too: He has seen them worn on the streets of Tokyo, and Todd Snyder recently unveiled a limited-edition version with an eye-catching plaid upper.
“Think of this pair as your everyday sneaker, but not one that you’ll wear at the gym,” says Tirabassi. “In other words, you want to keep these clean, sweat-free, and ready to show off.”
Instead of helping you work out, these men’s shoes will be your go-to pair when you need something comfortable but also stylish—on a long flight, for example, or while running errands around town.
“Whether they’re New Balance or Lanvin, almost every menswear label designs casual sneakers with their signature spin. No matter the budget, you’ll find one that speaks to you.”
Our Picks:
For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!
Danner boots have long been a favorite among outdoor explorers and people who work in rugged environments (the company got its start making boots for loggers in the 1930s). That list of fans includes a fictional British spy: In the upcoming James Bond film No Time to Die, Bond (played by Daniel Craig) sports a special pair of Danner Tanicus boots. And now you can grab some for yourself: The special-edition “007 Tanicus” boots Craig wears in the film will go on sale later this week.
The 007 Tanicus is an all-black version of the Tanicus boot, and it’s an obvious choice for someone like Bond, whose typical day can involve everything from white-knuckle car chases to leaping off cranes hundreds of feet in the air. The Tanicus is a lightweight military boot that’s built to perform in the most unforgiving environments. Its nylon-leather upper is crafted for superior durability, and it’s paired with a breathable mesh lining so your feet don’t roast when the temps climb.
Although it has a burly look, the Tanicus is designed to be as lightweight as possible and includes some key comfort features as well. It comes with a cushioned midsole to absorb impact forces and create a smooth, supportive ride, and the Vibram rubber outsole offers dependable grip on a variety of surfaces. Whether you’re battling ruthless villains or just running to the grocery store, your feet will stay comfy and protected.
Courtesy Image
That said, you might not want to get these boots dirty—they’ll be a unique collector’s item for Bond fans.
No Time to Die will be Daniel Craig’s fifth and final turn as 007 (a legacy stretching back to 2006’s Casino Royale), and the 007 Tanicus boots, complete with a commemorative box, will be an ideal way to memorialize his turn in the legendary film franchise.
Of course, if you want to buy them and take them hiking or hunting, they’re ready for that, too.
