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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 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 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 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.