20 Best Chelsea Boots for Men 2024

<p>Today’s Chelsea boots haven’t sacrificed looks for longevity, or vice versa. In fact, in the expansive and ever-evolving market of <a href=”https://www.esquire.com/style/mens-fashion/g40732397/best-mens-winter-boots/” target=”_blank”>men’s footwear</a>, Chelsea boots remain a curious anomaly: timelessly en vogue, differentiated from other <a href=”https://www.esquire.com/style/mens-fashion/g40732397/best-mens-winter-boots/” target=”_blank”>boots</a> by a shorter height and an elastic insert to keep them snug, the details that make all the difference. Some permutations have side zippers or feature a shaft that extends to the lower calf, but a close-fitting, pull-on ankle boot is pretty much the gist.</p><p>What makes best Chelsea boots boils down to your personal taste–and no matter what your taste, there’s a Chelsea boot to sate it. With that in mind, we’ve have gathered a slew of different options just ready for the picking.</p>”/>

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Huckberry

Best All-Weather Chelsea Boot

Blundstone Original 510 Chelsea Boots

Original 510 Chelsea Boots

Best All-Weather Chelsea Boot

Blundstone Original 510 Chelsea Boots

Blundstone is favorite here at Esquire, especially the 510 Chelsea boot. Why? Because of its buttery exterior that’s also able to keep your feet dry in all but the gnarliest of weather. It’s a shoe that you can wear in the rain, slush, or sun. It’s a shoe for every scenario.

Colors Black
Sizes 4-14
Materials Leather

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Best Classic Chelsea Boot

R.M.Williams Craftsman Leather Chelsea Boots

Craftsman Leather Chelsea Boots

Best Classic Chelsea Boot

R.M.Williams Craftsman Leather Chelsea Boots

R.M. Williams makes about as classic a Chelsea boot as you can get, Goodyear-welted sole and all. If you’re looking to invest in your first pair—or upgrade on a style that’ll always work with everything in your wardrobe—look no further than the aptly titled Craftsman.

Colors Brown, Black
Sizes UK 6-UK 12
Materials Leather

Best Burnished Chelsea Boot

Polo Ralph Lauren Bryson Leather Chelsea Boots

Bryson Leather Chelsea Boots

Best Burnished Chelsea Boot

Polo Ralph Lauren Bryson Leather Chelsea Boots

No one does cool, casual everyday elegance quite like Polo Ralph Lauren. In timeless shade of brown, these burnished leather boots have a classic silhouette, elastic sides for all-day comfort, and an easy, slip-on tab at the heel.

Colors Polo Brown
Sizes 7-15
Materials Leather

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best everyday chelsea boot

Greats Bowery Chelsea Boots

Bowery Chelsea Boots

best everyday chelsea boot

Greats Bowery Chelsea Boots

Greats has a Chelsea boot that looks the part, with some added flair. The slight platform gives these an extra edge, while the smooth, sleek, leather provides a luxe finish.

Colors Black
Sizes 7-12
Materials Leather

best chunky chelsea boot

Ted Baker Chunky Leather Chelsea Boots

Chunky Leather Chelsea Boots

best chunky chelsea boot

Ted Baker Chunky Leather Chelsea Boots

Now 30% Off

Pros
  • Round toe for extra comfort
  • Elasticated ankle panel adds stretch and flexibility
Cons
  • Limited color options

With a smooth leather finish and timeless elegance, these are the perfect go-to pair of classic, elevated Chelsea boots. And for a contemporary edge, the soles are ever-so-slightly platformed, giving these a subtly chunky look.

Colors Black
Sizes 7-13
Materials Leather

best all-occasion chelsea boot

Banana Republic Diego Leather Chelsea Boots

Diego Leather Chelsea Boots

best all-occasion chelsea boot

Banana Republic Diego Leather Chelsea Boots

For something stylish yet functional, BR has you covered. These leather Chelsea boots are so easy to style—jeans, trousers, and, hell, even chinos will love ’em.

Colors Brown
Sizes 7-13
Materials Leather

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best high-quality chelsea boot

Tecovas Chance Chelsea Boots

Chance Chelsea Boots

best high-quality chelsea boot

Tecovas Chance Chelsea Boots

Tecovas does cowboy boots to a T, and they’re taking their artisanship out of the warm, dry South and into the wet, cold winter weather with these Chelsea boots. Made from calfskin leather, these durable shoes have a slight heel and rounded toe for a chic look and all-day comfort.

Colors Brandy (Brown), Midnight (Black)
Sizes 8-14
Materials Leather

best unique chelsea boot

Thursday Boot Company Duke Chelsea Leather Boots

Duke Chelsea Leather Boots

best unique chelsea boot

Thursday Boot Company Duke Chelsea Leather Boots

Made from 100 percent leather, this burgundy style is an autumnal show-stopper, complete with shock-absorbing insoles.

Colors Black, Brown, Dark Olive Suede, Honey Suede, Chocolate
Sizes 6-14
Materials Leather

Best All-Black Chelsea Boot

Santoni Leather Chelsea Boots

Leather Chelsea Boots

Best All-Black Chelsea Boot

Santoni Leather Chelsea Boots

Now 40% Off

Far and few between are the outfits that aren’t elevated by a simple, classic black boot. Made from 100 percent leather, these chunky-soled Chelseas are an effortless and timeless adaptation staying true to the ’60s style.

Colors Black
Sizes UK 6-UK 8.5
Materials Leather

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most comfortable chelsea boot

Clarks Cologne Arlo 2 Chelsea Boots

Cologne Arlo 2 Chelsea Boots

most comfortable chelsea boot

Clarks Cologne Arlo 2 Chelsea Boots

Clarks is known for being one of the most comfortable, durable shoe brands out there. Good news—they have a damn good leather Chelsea boot, with a durable upper, stretchy side panel, and heeled sole.

Colors Black Leather, Tan Leather, Black Suede, Dark Sand Suede
Sizes 5.5-12
Materials Suede, Textiles

best waterproof chelsea boot

Ugg Biltmore Waterproof Chelsea Boots

Biltmore Waterproof Chelsea Boots

best waterproof chelsea boot

Ugg Biltmore Waterproof Chelsea Boots

Now 33% Off

Pros
  • Waterproof
  • Plush insoles
Cons
  • More of a casual look

All the coziness and warmth of Uggs, but with the style of a Chelsea boot. Plus—they’re waterproof!

Colors Black, Chestnut Suede, Dark Olive Suede, Dusted Cocoa
Sizes 7-15
Materials Leather, Textiles

best cushiony chelsea boot

Magnanni Monza Chelsea Slip On Boots

Monza Chelsea Slip On Boots

best cushiony chelsea boot

Magnanni Monza Chelsea Slip On Boots

Crafted from Italian leather, these boots are an investment piece you’ll reap the rewards of for years to come. They’re waterproof, stylish, and oh-so cushiony.

Colors Brown
Sizes 7-13
Materials Leather

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best chelsea boot under $100

Calvin Klein Brayden Chelsea Boots

Brayden Chelsea Boots

best chelsea boot under $100

Calvin Klein Brayden Chelsea Boots

Affordable and suave, Calvin Klein’s Chelsea boot is the perfect pick for a dressier look—without the high price tag. The pointed toe on this style is a surefire elevated vibe, while the leather sole will last you many winters to come.

Colors Black Leather, Black Saffiano
Sizes 7-12
Materials Leather

best chelsea boot under $50

Amazon Essentials Chelsea Boots

Chelsea Boots

best chelsea boot under $50

Amazon Essentials Chelsea Boots

Need a Chelsea boot in a pinch? Amazon Essentials has a style that you can get via Prime within a few days—it looks and feels the part of an elevated shoe, too.

Colors Black, Black Faux Leather, Chestnut Brown, Dark Tan
Sizes 7-13
Materials Faux Suede, Faux Leather

Best High-Fashion Chelsea Boot

Bottega Veneta Tire Chelsea Boots

Tire Chelsea Boots

Best High-Fashion Chelsea Boot

Bottega Veneta Tire Chelsea Boots

Over the past few years, Bottega Veneta really brought its A-game when it comes to footwear, dropping styles—particularly its collection of bright, eye-catching boots—that fashion insiders and followers are coveting. Lewis Hamilton knows what’s up.

Colors Blue
Sizes IT 39-IT 41.5
Materials Leather, Rubber

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Best 100% Leather Chelsea Boot

CamperLab Walden Ankle Boots

Walden Ankle Boots

Best 100% Leather Chelsea Boot

CamperLab Walden Ankle Boots

Now 40% Off

Burnished yellow leather sets this Chelsea boot apart. And, because it’s CamperLab, the quality speaks for itself.

Colors Yellow
Sizes IT 39-IT 46
Materials Leather
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