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The best Chelsea boots to complete the stylish man’s cold-weather look

Here are the best mens Chelsea boots for 2024

Chelsea boot in the woods
Hamza Bounaim / Unsplash

On the list of best boots that any man can and should own, the Chelsea boot is near the top. They are some of the most stylish, thanks to their many different colors, patterns, and materials. They are some of the most convenient thanks to their laceless design. And they are some of the most versatile thanks to their dressed-up or dressed-down ability. Swap these out for your dress shoes or your sneakers for the most masculine looks you will get.

The Rolling Stones in 1964.
Ron Harvey / Everett Collection Inc / Alamy Stock Photo

Chelsea boots and their musical influence

While most men’s clothing, shoes, and accessories trace their origins back to the military in some way, Chelsea boots are one of the few that don’t. While they were originally designed specifically as shorter and more convenient riding boots in Victorian England, they didn’t gain their current popularity until the sixties, when the country’s rock and roll community began adopting them.

All throughout the streets of London acts like The Beatles and The Rolling Stones could be seen wearing them on and off stage as the newest and the hottest fashion trend. Paul McCartney and John Lennon took them one step further when they commissioned a higher Cuban heel and a pointy toe to create a specific chelsea boot known as the Beatle Boot. They may be a symbol of versatility now, but they are the bedrock of British Invasion style.

Florsheim Whitmore

Florsheim Whitmore

When you are looking for the best chelsea boot, it is best to start with one that is the most versatile. The Whitmore from legendary shoe company Florsheim has the perfect look that can take you from the office to the work site to date night. Wear this boot with a pair of jeans and a sweatshirt or chinos and a sportcoat and you will never not be in style.

Taft Dylan in Salt

TAFT Dylan in salt

Look, you can always go basic, run-of-the-mill, middle-of-the-road. You can keep it simple and versatile. Or you can do so much better. There isn’t a brand on this planet that is more equipped to help you do better than TAFT. With their one-of-a-kind designs and their custom options, you can go truly unique with your chelsea. The Dylan in the salt colorway will stand out in every way this spring. Create a custom belt to go with it, and you will have the best look you’ve ever had.

Amberjack gray suede

Amberjack gray suede

If you don’t know anything about these shoes, knowing that Aaron Rogers is deeply involved with these boots is enough. If they are good enough for the former NFL MVP and future NFL Hall of Famer then they are good enough for us. Luckily, we know more, so much more. Water repellant suede, athletic sole, and made to feel as good as they look means they are the best you can find in hybrid Chelseas.

Thursday Boot Harness
Thursday Boots

Thursday Boot Harness

Men’s style is about attitude. Sometimes, it is about showing you don’t have one (being presentable and respectful in a suit and tie), and other times, it is about showing you have one (not a pushover and ready for business). The Thursday Harness, with its distressing on the toes and o-ring design, is the perfect way to show the exact right amount of attitude.

Common Projects Chelseas
Mr. Porter

Common Projects Sand Suede Chelsea Boot

Common Projects’ mastery of everyday essential footwear is unrivaled, and that applies to their version of the Chelsea boot. Available in a tan suede that’s become basically synonymous with the best Chelsea boots in recent years, they feature a crepe sole that’ll keep you comfortable wherever the night takes you.

Beckett & Simonon Preston
Beckett & Simonon

Beckett Simonon Preston Chelsea Boot

Beckett Simonon only does made-to-order footwear but they do it at a very approachable price — like half of what you would expect from a traditional cobbler. The Preston features a fuller, more rounded toe and a chunkier sole and heel than your traditional Chelsea. They’re perfect for someone who likes the lace-up workwear look but wants to try a Chelsea. If you’re willing to wait a month or two for their production process, you can’t beat the quality for under $300.

Robert August The Fulton St
Robert August

Robert August Fulton St Chelsea Boot

Robert August shoes are completely customizable. Their Fulton St Chelsea boot is a classic Chelsea design that you can have made in a wide range of colors and fabrics and add pretty much any kind of sole you want. The version featured above is model no 4516, featuring camel suede and a white Vibram alpine sole. It’s a modern interpretation of the classic that will complement your entire wardrobe.

Chelsea boots were made famous by rock stars, but anyone can wear them with practically any wardrobe today. Whether you wear jeans every day or still have to wear a suit to work, you could wear a pair of chelsea. They’re the most refined way to wear boots, and yet they’re also the easiest way. Most men will find brown leather the easiest to fit into their wardrobe, but black is the classic look, especially with suits. Going with suede will provide a different texture that will age really nicely. Don’t shy away from a light gray or sand color suede — they’re easy to clean and look amazing with denim or black pants. Whichever color or material you go with, we’re pretty sure that Chelsea boots will be your new favorite footwear.

Editors' Recommendations

Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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