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The Best Men’s Chelsea Boots To Wear Right Now

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Photo: Thursday Boots Cavalier

Popularized by Englishmen (and women) throughout the ’60s, the Chelsea boot makes for a silhouette that has surely stood the test of time. While they grew popular throughout Great Britain (and later around the globe), the boot’s name is a product of its environment, as Chelsea was and still is one of London’s trendiest neighborhoods. For further confirmation of their popularity, the most famous Brits at the time had a strikingly similar style of boots made in their name; here’s a hint, they start with “B” and end with “eatle Boots.” Nowadays, Chelsea boots have transcended into an immensely common piece of footwear — one we think should be in every man’s wardrobe. With countless budget options and knock-offs in the mix, it could be impossible to narrow down exactly which brand is right to choose — but we’ve gone ahead and made it easy for you by rounding up the best men’s Chelsea boots.

The Best Chelsea Boots

Chelsea Boot considerations

Material: Most people want their boots to be able to stand up to tough conditions. But since Chelsea boots have more of a fashion slant, leather and suede are popular materials. This doesn’t mean they can’t be durable and taken out into rougher terrain, but they’re generally preferred for style over function. That’s why it’s important to decide if you’d like some water protection on your boots, which you can do yourself if they don’t come with that.

Design: Chelsea boots have an iconic silhouette, characterized by being low to the ground, just above the ankle, and having a tab (or two) to maneuver them. But different labels will shake things up here and there, taking inspiration from ranch boots or work boots, for example. Elastic, or some kind of stretchy fabric on the side of the boot is also a key ingredient.

Dr. Martens 2976 Chelsea Boot

  • Lightweight
  • Goodyear welted
  • Might hurt while breaking them in

The Classic: Kicking off a list like this, everyone should already know the drill. Though their backstory is polarizing, Doc Martens has been embraced by countless counter-cultures over the past five decades. Docs are pragmatically the Converse of boots, and the 2976 silhouette is the quintessential Chelsea boot, providing that classic ’70s look that never goes out of style. More or less, everything else is as expected right down to the Goodyear Welted leather construction, and what you see is what you get with a brand as renowned within their circle as Doc Martens. After all, he’s a doctor.

Thursday Boots Cavalier

  • Shock-absorbing heels
  • Sustainably built
  • A little narrow
  • No loops

The Safe Pick: The qualifications that land a boot a spot on this list can be dubbed “The 3 Cs” and read as follows: Comfy, classy, and Chelsea. Oh, make that 4: Cavalier. While all of Thursday Boots’ options are worth a look, the Dusty Brown Suede colorway makes for a sustainably stylish couple of stompers from a brand admittedly willing to fight the big industry prices. Thursday’s Cavalier Boots make for a great pair on every day of the week and are built for your busiest days, as the New York-bred brand might know about being busy better than anyone else.

Blundstone Chelsea Boots

  • Weatherproof
  • Slip-resistant outsole
  • Heels may wear down with prolonged use

The Best Outdoor Chelsea Boots: As an O.G. within their industry, Blundstone has surely progressed with the times, putting forth a pretty stylish boot that you won’t worry about dirtying up. As a matter of fact, they’re crafted with the expectation of getting a little messy. With many models to choose from, few match the stylistic simplicity of their classic 510, providing a stable, long-lasting boot built for harsh weather that can provide you with grit and glitz altogether.

Danner Bull Run Chelsea Wedge Work Boots

  • Made in USA
  • Comfortable during for long days
  • Run small
  • Smell can build up if not cleaned regularly

The Best Work Chelsea Boots: “Made for wear and tear” and “Made in the USA” are a pair of phrases that have grown synonymous at this point; luckily, Danner is one of many brands that distinguish the difference between synonymous and monotonous. With stitch-down construction for durability’s sake, the Portland-based Bull Run offers immense traction and easy on/off, making them yet another great addition to Danner’s broad selection of rugged footwear.

Tecovas The Chance

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  • Made in Leon, Mexico
  • Easy to maneuver
  • Run big

The Best Western Inspired Chelsea Boots: Marrying the best of the Chelsea boot’s style and function with a western slant (specifically Texas), The Chance from Tecovas is a versatile urban boot. Designed in Austin, Texas, and made in Leon, Mexico, these boots have the classic Chelsea silhouette with a western-inspired leather sole, and Goodyear welt construction. These boots fit right in with a pair of jeans, whether they’re for the ranch or for the city.

Beckett Simonon Bolton Boots

  • Built to last
  • Quality leather
  • Need to treat for rain (if you do want to worry)

The Comfiest Chelsea Boots: Tired of getting your Achilles heel gnawed at while trying to break in a new pair of boots? Look no further, as these are practically like a pair of Vans, giving wearers virtually no trouble when walking into that one friend’s place who is way too uptight about their carpet. The Bolton Boots are made out of pure calfskin, worth every penny, and, surprisingly, don’t cost a baffling amount of them.

Common Projects Suede Chelsea Boots

  • Cushioned rubber soles
  • Made in Italy
  • Only available in whole sizes

The Best Suede Chelsea Boots: Common Projects is a brand that can be found along various walks of life, be it an upscale wedding or a low-key night out. Worn by rapper-turned-shoe-salesman Kanye West himself, the Suede Chelsea Boots garner a solid stamp of approval as far as staying fashion-forward is concerned. And, just in case Ye’s name isn’t enough of a stamp, the brand’s signature series number is subtly printed in gold by the heel. Sold in a neutral tan colorway as well as chocolate brown, these almond-toed boots were hand-stitched in Italy, as goes for each of the brand’s pairs.

R.M. Williams Comfort Craftsman Suede Boots

  • Rugged yet stylish
  • May have to weatherproof

The All-Arounders: The Australian-bred R.M. Williams is famous for its Chelsea boots, so this should be a no-brainer. However, they do offer a variety of other quality clothing that would pair perfectly with the former. Take it as a business tactic. Founded by the man who shares its namesake, Williams was merely a swagman until ultimately growing into an esteemed name and brand. Their Comfort Craftsman Suede boots are meticulously crafted from Goodyear-welted leather, a couple of pull tabs, and all that good stuff for a fraction of the cost that brands who do the very same charge. Choose from a trio of colors and wear them with the coolest jeans you have.

Tricker’s Henry Country Dealer Boot

  • Made in England
  • Trusted quality
  • High-end quality means high-end price

The Prime Pick: As England’s longest-tenured shoemakers, the lads at Tricker’s have been crafting country boots since 1829, which is practically two centuries at this point. Their Henry Country Dealer Boot evokes their start, built on their original Commando sole that was curated with the damp countryside in mind. Sold in three rustic colors, these storm-welted steppers have a dual tab for ease and were put together with nothing but some of the finest leather, as you’d expect getting this deep into the list.

 A.P.C. Charlie Boots

  • Made in Portugal
  • Great for formal or outside situations
  • Square toe might not be for everyone
  • Runs small

The Best Chelsea Boots for Rain: With glazed calfskin, these manage to shine through rain, snow, or sleet. Akin to their denim — and catalog in its entirety — these A.P.C. boots are formidable, pricey, and stylish as hell. Never one to necessarily push the envelope, the Parisian off-the-rack brand keeps things elegant and direct, simple and shining. These slightly-square-toed dress Chelseas will get you through whichever black-tie event you find yourself attending next. The Charlie Boots run one size small, so make sure to take it down a notch to prevent ending up with purple feet; even then, these might still be worth it.

The Best Field Jackets to Complete the look

Photo: Buck Mason

To complement your rugged and stylish look, a jacket with similar qualities is a good start. Our best field jackets guide can help you out.