The Best Chelsea Boots for Men

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, 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 a 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.

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

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. Your choice of three widths helps ensure a better fit, but these won't feel like sneakers.

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

Rhodes' Blake Boot is a 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.

Plus, 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.

Popularized by Kanye West in the mid-2010s, Common Projects's suede Chelseas pushed the style into the mainstream, even if they've been around since the 19th century.

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 small gold foil number logo on the outer heel, 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.

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.

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.

That's because it embraces 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 ubiquitous.

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

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

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.

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

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.

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.

Knit from a blend of RWS-certified merino wool and recycled plastic bottles, Rothy's The Chelsea Boot isn't really a Chelsea boot at all. In fact, it's barely a boot — or, at least it barely feels like a boot. It's soft but still supportive, warm while being breathable. It's like the best sock ever, applied to a sturdy, non-slip outsole.

Sure, fabric doesn't offer the same protection as, say, leather, but on the bright side, if the knit uppers get dirty, these can go through the wash.

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.

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.

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.

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 Boot. Available in five colors, every pair is hand-crafted and -lasted in Albacete, Spain.

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.

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

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 the heel of the boot.

These are also Goodyear welted and based off 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.

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.

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.

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 a worker works.

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

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.

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. Plus, this Doc Marten 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 your faster to your preferred state in these.

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.

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 two colors and sizes 8 through 14.

These work well with jeans or slacks, courtesy of its tight top, which fits snug unlike an engineer boot. 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.