The 20 Best Chelsea Boots to Buy Now and Cherish Always (2024)

When it comes to a Chelsea boot that'll offer the most bang for your buck, it's undoubtedly New Republic's Sonoma, the brand's signature style. This one in sleek tan suede, completely devoid of flourishes, features a crepe outsole and padded insole. It looks like a designer option that should cost a pretty penny, but it's priced at under $100. Again, under $100!

Made-in-Italy shoes are some of them best, which is why they often come at a steep price. This, however, does not apply to Astorflex, a brand that offers incredible Italian-made Chelsea boots that won't break the bank.

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.

C'mon—you knew the Docs would show up in here eventually! After all, you can't really talk about British footwear (or, modern footwear in general, really) without spotlighting the ultimate boot makers.

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.

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.

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.

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.

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.

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.

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

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.

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.

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

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.

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.

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.

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.

If there's any brand that has expertise in the traditions of English horseback riding—and the footwear required for it—it's Burberry. Crafted from calf leather and a signature checked panel, these are the Chelsea boots for the man who knows what he's doing.

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