The Best Chelsea Boots for Men

Chelsea boots originated in England in the mid-19th century. Then, they were called “Paddock boots,” a short men’s boot style for equestrian functions. They’ve only strayed from home — and horse riding — just recently. The elasticized wonders were a staple in mid-’60s London scenes and protected the feet of seemingly every British invader — from John Lennon to Ringo Starr. Recently, they’ve seen a revival on many of menswear’s best-dressed.

That goes for guys who style them with suits as readily as it does for those who prefer tapered jeans. Like other menswear essentials with a storied history – from the field coat to the trucker jacket to the ever-ubiquitous henley – Chelsea boots are (when done right) the footwear equivalent of a seriously cool piece every guy can look great wearing.

To learn more about our testing methodology and how we evaluate products, head here.

Zappos

Best Overall Chelsea Boots

Best Overall Chelsea Boots: Blundstone BL558 Boots

• $219.00 at Zappos

• Country of Manufacture: China, Vietnam, Mexico, Thailand
• Upper Material: Leather
• Outsole Material: Rubber
• Welt Construction: Cemented sole

Technically part of the Australian bush boot lineage of boots, Blundstone’s 558 boot is one of the best values you can get. It’s a top choice for people in every industry thanks to the tough leather upper, shock-absorption and classic design.

On foot, they feel comfortable from the first wear, thanks to the built-in EVA footbed with extra XRD tech — which is essentially reactive cushioning — in the heel cup. These will wear like sneakers, which is why people wear them like sneakers. They’re everywhere — and for good reason, clearly.

Nothing’s gone wrong with these in the four years they’ve owned them, our tester says: mild cracking, little to no cosmetic damage and the gussets are as elasticated as they were on day one. Plus, while the tread is slowly wearing down, it’s still in pretty good shape, our tester says.

Take it from this writer, who’s worn Blundstone boots consistently for about five years as well: These are about as durable as it gets at key stress points, and they’ve developed an even cooler brown leather patina over time.

Read more about this brand in our guide to Blundstone boots.

R.M. Williams

Best Upgrade Chelsea Boots

Best Upgrade Chelsea Boots: R.M. Williams Craftsman Boot

• $495.00 at

• Country of Manufacture: Australia
• Upper Material: Leather and suede
• Outsole Material: Rubber
• Welt Construction: Goodyear welt

R.M. Williams’ Craftsman Boot is its best-selling boot, braving the Australian outback on the feet of its hardest-working cowboys. The single, one-piece leather upper is supple yet durable and the Goodyear-welted construction extends the life of the boot several factors over.

These surely won’t be as soft on your feet as Blundstones, because of the leather sole, but they’re dress boots after all. In fact, there’s some debate as to which boot brand is more beloved in Australia, at least from what this writer has heard. The consensus, though, seems to be that each is useful in a well-curated wardrobe.

Plus, with R.M. Williams, your choice of three widths helps ensure a better fit – keep in mind that these won’t feel like sneakers, though.

That being said, if these are tough enough for Aussie cowboys, they’re tough enough for you.

Huckberry

Best Affordable Chelsea Boots

Best Affordable Chelsea Boots: Rhodes Blake Boot

• $198.00 at Huckberry

• Country of Manufacture: Mexico
• Upper Material: Suede or waxed cowhide
• Outsole Material: Lightweight Meramec PU
• Welt Construction: Recraftable welt

Rhodes’ Blake Boot is a rugged-meets-refined take on the Chelsea style. It’s cut from full-grain roughout leather, situated atop a PU cushioned outsole and finished with elasticated gussets.

Like most things that come from the pages of Huckberry (as with the Rhodes Footwear line), this style is fit for plenty of rugged adventures or casual log cabin weekends. Yet, style-wise, it wears just as well with black or blue jeans back in town.

It’s fully lined with leather and made in Leon, Mexico, the Mecca of shoemaking in Mexico. That means these boots will stand tall from the first wear, and last longer even through constant use. Our tester found these were especially comfortable at the toe, where the rounded shape gives them enough room to space out without sliding around.

Red Wing

Best American Made Chelsea Boots: Red Wing Heritage Classic Chelsea 3194 – Black Harness

• $300.00 at franklinandpoe.com

• Country of Manufacture: U.S.A.
• Upper Material: S.B. Foot Tanning Black Harness leather
• Outsole Material: Traction Tred
• Welt Construction: Goodyear welt

If you’re looking for a classic black Chelsea and want something that more substantial and better quality than ubiquitous boots from Down Under, get these Chelseas from Red Wing Heritage. They have the same profile you know and love, but are built to last for decades.

They feature a lined leather upper from Red Wing’s own S.B. Foot Tanning Company, a leather insole and a forgiving Traction Tred outsole. Unlike the competition, they can also be resoled and rebuilt after years of use.

Sure, they cost more and have a longer break-in period, but they’re just a better investment in the long term.

Oak Street Bootmakers

Best Goodyear Welt Chelsea Boots

Best Goodyear Welt Chelsea Boots: Oak Street Bootmakers 5504 Chelsea Boot

• $498.00 at

• Country of Manufacture: United States
• Upper Material: Chromexcel leather
• Outsole Material: Studded Dainite rubber
• Welt Construction: Goodyear welt

Constructed from Horween Chromoexcel, a leather made using proprietary techniques, Oak Street Bootmakers’ made-in-USA 5504 Chelsea Boots are better once broken in.

Go a half size down to allow them to stretch to your foot, and ready yourself for some of the finest patina you can find.

That’s thanks to the brand’s emphasis on quality hides, but also its commitment to proper craftsmanship. These are hefty boots, but not without cause.

Just don’t wear too thick of a sock when breaking them in, no matter how badly you want to. Like we said, these will stretch, and you want them to stretch to your true size, but not beyond it.

Unmarked

Best Black Leather Chelsea Boots

Best Black Leather Chelsea Boots: Unmarked Chelsea Toro Special Edition

• $290.00 at

• Country of Manufacture: Mexico
• Upper Material: Gold-rated black leather
• Outsole Material: Rubber Minilug outsole
• Welt Construction: Goodyear storm welt

Both Fair Trade and Gold-rated, markers of both quality and environmental consciousness, Unmarked’s Special Edition Chelsea Toro boots are made from 2.2 mm leather uppers, calf leather liners and a vegetable-tanned footbed with cork cushioning.

There’s an impressive level of care that have gone into these boots, as evidenced by the detailed specs. Plus, the outsole, which was entirely hand-shaped, can be replaced when it wears down. What’s most impressive about these, though, is the overall darkness of its tone. These are truly all-black.

Courtesy

Best Weatherproof Chelsea Boots

Best Weatherproof Chelsea Boots: Nisolo All-Weather Chelsea Boot

• $195.00 at nisolo.com

• Country of Manufacture: Peru
• Upper Material: Waterproof leather
• Outsole Material: Lightweight waterproof rubber
• Welt Construction: Stitchdown

Although all of the suede (and most of the leather) boots on this list wouldn’t survive a light rain, Nisolo’s All-Weather Chelsea Boot is built to survive a torrential downpour — and then some.

That’s not the only thing to love about ‘em, as Nisolo makes its boots ethically in factories with high standards, fair treatment and living wages. The fact that you’re getting a handsome yet useful boot is icing on the cake.

The studded rubber sole provides traction, while the water-resistant leather upper keeps your feet dry.

MR PORTER

Best Suede Chelsea Boots: Common Projects Suede Chelsea Boots

• $525.00 at MR PORTER

• Country of Manufacture: Italy
• Upper Material: Suede
• Outsole Material: Crepe rubber
• Welt Construction: Stitchdown

Common Projects’s suede Chelseas pushed the style into the mainstream, even if the silhouette has been around since the 19th century.

The gold foil serial number on the heel gave these boots a distinct edge, an instant sign that you were in the know by wearing a pair (and dropping the requisite cash). The availability of the boots in a mix of both cool and earthy tones was also a nice plus, as they wore well with everything from light wash jeans to black trousers.

Now, everyone from Harry Styles to Jason Theroux wears these, making them as popular as they are nondescript. To match the soft suede upper, there’s a tonal crepe sole and tonal elasticated gussets.

The crepe sole is super comfortable, but it’ll go fast, making these essentially unwearable after that. Keep that in mind when dropping the $525. These shouldn’t be daily drivers.

Amazon

Best Common Projects Alternative

Best Common Projects Alternative: New Republic Sonoma Suede Chelsea Boot

• $99.00 at Amazon
  $128.00 (23% off)

• Country of Manufacture: China
• Upper Material: Suede
• Outsole Material: Crepe
• Welt Construction: Single-stitch flat welt

Skeptical about the Chelsea boot category? New Republic’s Sonoma Suede Chelsea Boot lowers the point of entry, both through price and palatability.

That means inventory can move quickly, so keep an eye on these boots. That being said, they’re about as close as it gets to Common Projects (in a great way) without spending more than $500.

They’re cut from soft suede, lined with leather, and finished with tonal elastic gussets and pull tabs. Plus, a padded insole — on top of the crepe outsole — ensures comfort.

Oliver Cabell

Best Minimal Chelsea Boots

Best Minimal Chelsea Boots: Oliver Cabell Chelsea Boot

• $248.00 at

• Country of Manufacture: Spain
• Upper Material: Italian suede
• Outsole Material: Crepe
• Welt Construction: Hand-stitched

Oliver Cabell makes a bunch of minimal, easy-to-wear sneakers. A few years ago, they expanded to boots, beginning with their suede and crepe-soled Chelsea boots. Available in five colors, every pair is hand-crafted and -lasted in Albacete, Spain.

It’s designer quality without the mark-up, and you can score deals from time to time on Oliver Cabell boots – in addition to the agreeable low price from the get-go.

The crepe sole, as mentioned above, means comfort, but not forever. The material wears down faster than traditional leather or rubber insoles but beats them in terms of true comfort.

Zappos

Best Overall Blundstone Boot

Best Lug Sole Chelsea Boots: Blundstone Lug Boot

• $235.00 at Zappos

• Country of Manufacture: China, Vietnam, Mexico, Thailand
• Upper Material: Leather and textile
• Outsole Material: Lug rubber
• Welt Construction: Cemented sole

The Blundstone Lug Boot is a riff on the brand’s work boot, which has a heftier outsole than the regular Chelsea. This all-new style is a fusion of both designs that offers better tread, a softer, more cushioned ride and a comfortable, compact interior. Think of this as your usual Blundstone boot, but upgraded.

Blundstone boots were a true Tasmanian work boot, after all, and while they might be ubiquitous among trend-setting dressers these days, some extra traction is always welcome.

These boots embrace parts of Blundstone’s popular Work Boot, which has a protective toe, this same chunky outsole and an enhanced footbed.

Our tester found these to be better than the traditional Blundstones, but not for the same sort of pedestrian routines most people put Blundstones through. These are the top model, even if others are more widely seen.

Learn more about the all-new Lug Boot in our Blundstone brand head-to-head review.

Courtesy

Best Western-Style Chelsea Boots

Best Western-Style Chelsea Boots: Tecovas The Chance

• $235.00 at tecovas.com

• Country of Manufacture: Mexico
• Upper Material: Full-grain calfskin, bovine or suede
• Outsole Material: Leather
• Welt Construction: ¾ Goodyear welt

Tecovas might specialize in cowboy boots, but The Chance is an excellent Chelsea. It has a slight heel, a short shaft and a rounded toe. Plus, it comes in four colors and sizes 8 through 14.

Think of them like an alternative to Western-style boots when you still want a touch more flair than a traditional dress Chelsea boot. And since Tecovas boots are all the rage right now and the brand seems to be growing at a steady clip, they now come in a cool Rust Suede option for a touch more refinement.

These work well with jeans or slacks, courtesy of its tight top, which fits snug. It may take a second to adjust to the heel, our tester says, but no more than a few wears.

Learn more about this brand in our guide to Tecovas boots.

Unmarked

Best Upgrade Western-Style Chelsea Boots: Unmarked El Torino Boots Dark Sand

• $390.00 at unmarked.mx

• Country of Manufacture: Mexico
• Upper Material: Suede leather
• Outsole Material: Leather
• Welt Construction: 120 degree welt (mini welt) with brass nailed/wooden pegged waist

Handmade Punto Marcado, these boots are all Western style with the ease and wearability of a Chelsea. The suede upper with a multicolor toe bug embellishment set these apart visually, but the manufacturing is also top notch.

These boots feature a a full leather insole with carved channels, a full stacked leather heel, a leather heel counter and a 120 degree mini welt.

They come in a variety of leathers ranging from suede to bovine to bison. To note: they’re built on demand and will ship within 15 to 30 days of ordering.

Saks Fifth Avenue

Best Outdoor Chelsea Boots

Best Outdoor Chelsea Boots: Diemme Balbi Suede Ankle Boots

• $370.00 at Saks Fifth Avenue

• Country of Manufacture: Italy
• Upper material: Suede/rubber
• Outsole material: Rubber
• Welt construction: Molded/rubberized

As the category has grown, interesting streetwear-inspired riffs have popped up, oftentimes to the dismay of traditionalists. These reference a mix of influences, combining a thick rubber outsole and midsole, with an elevated suede and elastic upper.

The front also plays off the classic Duck boot design, but with more of a streetwear edge. The suede upper, on the other hand, is a style move not typically seen on most winter (or winter-leaning) boots.

They’d be great for visiting Aspen, but probably not summiting a mountain. Think of them like most outdoors-inspired streetwear goods: they’re more for show than they are actual performance. But these boots are well-made nonetheless, and they’re pretty damn comfortable, too.

Nordstrom

Best for the Open Road

Best Chelsea Boots for the Open Road: Belstaff Longton Leather Chelsea Boot

• $395.00 at Nordstrom

• Country of Manufacture: Portugal
• Upper material: Leather
• Outsole material: Rubber
• Welt construction: Cemented sole

There are few Chelsea boots simpler than Belstaff’s Longton style — but that’s a good thing. The smooth leather upper matches the matte rubber sole, which lends comfortability without looking too casual. These have your standard two-tab top and a contrasting leather liner inside.

Plus, if you’ve been looking for sturdy yet accessible boots to wear with your Belstaff jacket on road trips or seasonal adventures, there’s hardly a better move than to get some rugged Belstaff boots with the requisite functionality and style.

Huckberry

Best Hybrid Chelsea Boots

Best Hybrid Chelsea Boots: Danner Tramline Chelsea 917 in Roasted Pecan

• $210.00 at Huckberry

• Country of Manufacture: United States
• Upper material: Nubuck leather
• Outsole material: Vibram
• Welt construction: Modernized stitchdown

Sliding into a pair of Danner boots carries with it an aura of history – seriously. The famed Pacific Northwest brand made boots for loggers and true men of action, and they drew on that heritage to offer this modern, hybrid Chelsea boot.

Inspired by 1930s caulked logger boots, these should prove substantially more comfortable, all thanks to a Vibram midsole and a Danner-exclusive Vibram outsole with a sneakerboot-esque build.

Courtesy

Best Formal Chelsea Boots

Best Formal Chelsea Boots: Beckett Simonon Bolton Chelsea Boots

• $239.00 at beckettsimonon.com

• Country of Manufacture: Colombia
• Upper Material: Full-grain calfskin leather
• Outsole Material: Leather
• Welt Construction: Blake stitching

Made to order, Beckett Simonon’s Bolton Boots are the prototypical Chelsea.

The elasticated gusset extends from heel counter to the top, making them easy to take on and off, but the shaft is made from full-grain calfskin leather sourced from a gold-rated tannery based in Italy, which is the highest rating a tannery can be given. That makes these high quality but also less impactful on the environment.

As luck would have it, they also feature streamlined toe shape that makes them an ideal alternative to black dress shoes — even the leather has an elevated shine to it. Take a page from The Beatles’ playbook (never a bad move) and style them with a suit.

Courtesy

Best Brown Leather Chelsea Boots

Best Brown Leather Chelsea Boots: Grant Stone Chelsea Boot

• $380.00 at grantstoneshoes.com

• Country of Manufacture: China
• Upper Material: Horween Chromexcel
• Outsole Material: Micro-stud rubber
• Welt Construction: Goodyear welt

Made from Horween Chromexcel leather, Grant Stone’s Chelsea Boot features full-grain leather heel counters, insole and liner, a micro-stud rubber outsole and a single pull tab on the heel of the boot.

Horween Chromexcel is some of the best and most sought-after leather on the market, and it makes for Chelsea boots in a unique shade that should prove reliable for frequent wear.

These are also Goodyear welted and based on a UK last. As such, folks should order a half size down from their US standard. A size 10, for example? You need a 9.5 in these.

Zappos

Best Rubber Chelsea Boots

Best Rubber Chelsea Boots: Hunter Original Chelsea

• $160.00 at Zappos

• Country of Manufacture: China
• Upper Material: Rubber and polyester
• Outsole Material: Rubber
• Welt Construction: Rubberized

Ideal for really rainy days, Hunter’s Original Chelsea mixes the practicality of a tall rain boot with the compactness of a Chelsea, creating a boot that protects while being plenty mobile. When on, these are comfortable, even though your foot will slide back and forth if you’re between sizes. That won’t be enough to generate blisters, but it’ll annoy, especially if you’re wearing thin socks.

If you’re the type who wants a more streamlined style – AKA a Chelsea boot, versus a pair of taller-than-average rain boots or galoshes – these could prove an optimal style. That being said, since they’re more of a rain boot than a true Chelsea boot, they’re sometimes difficult to dress up properly.

These are also particularly warm, which means you’ll sweat if you’re out there struttin’.

Explore more waterproof options in our rain boot buying guide.

Huckberry

Best Artisan-Made Chelsea Boots

Best Artisan-Made Chelsea Boots: Adelante Mendoza Chelsea Boot

• $265.00 at Huckberry

• Country of Manufacture: Guatemala
• Upper Material: Full-grain leather
• Outsole Material: Vegetable-tanned leather with rubber protector
• Welt Construction: Goodyear welt

Adelante is impressive for two reasons: For one, the brand’s boots are really well made. And they’re made by craftsmen in Guatemala that are paid through the Living Well Line, an international standard that defines what a well above minimum wage is – wherever it is that a worker, well, works.

They’re responsible for inserting the reactive memory foam footbed, finishing the stacked leather outsole and applying the all-leather uppers.

It’s an uncommon approach in the footwear world, but the thing is, the shoes hold up to repeat wear, look great in a variety of style situations and feel soft out of the box (thanks to the leather lining, among other details).

They’re why these boots feel comfortable, fit well and last a long time. As such, it’s only fair — in fact, it’s downright right — that they’re compensated correctly for their work.

Dr. Martens

Best Throwback Chelsea Boots

Best Throwback Chelsea Boots: Dr. Martens 2976 Bex Smooth Leather Chelsea Boots

• $180.00 at Dr. Martens

• Country of Manufacture: China
• Upper Material: Leather
• Outsole Material: Synthetic rubber lug
• Welt Construction: Goodyear welt and reinforced stitch

This is the ideal chunky Chelsea boot, according to stylist Vanessa Powell. It’s sleek and black and basic from above, but the shoe stands out at your side profile.

Better still is the fact that these harken back to retro style eras while fitting right in with current trends – will Dr. Martens ever truly go out of style? Time will tell, one might say.

Plus, this pair is more comfortable than the lace-ups you’ve come to associate the brand with. Sure, there’s a decent break-in period, both for the uppers and the outsole, but you’re faster to your preferred state in these.

Huckberry

Most Versatile Chelsea Boots

Most Versatile Chelsea Boots: Astorflex Bitflex

• $250.00 at Huckberry

• Country of Manufacture: Italy
• Upper Material: Premium leather
• Outsole Material: Natural crepe rubber
• Welt Construction: Stitchdown

Astorflex’s Bitflex boots are soft from the first wear, courtesy of the boot’s primary material, a leather that’s been aged for a month in a mixture of water, oak bark and powdered mimosa.

The bath is all-natural and it ages the leather ever so slightly to make these more comfortable, for longer. The process, and the rest of the boot’s construction, is done by a small-time bootmaker in northern Italy.

The leather has a pleasing texture that stands out nicely beneath most pants, especially garment-washed chinos you might wear in a business casual situation. And while some dressy leather Chelsea boots might look out of place with denim, these play just fine with indigo selvedge or olive five-pocket pants – talk about versatility.

As for the chassis, it’s a 100 percent natural crepe rubber sole, an outsole renowned for its comfortability but discounted for its quick disintegration. It won’t go in weeks, but don’t expect the soles to last a decade.

Related Topics