8 Chelsea Boots That Will Transform Your Look

There's something so inherently cool about Chelsea boots. They're a little punk, a little princely—and now they're seemingly everywhere. Herewith, a guide for navigating the now-full-blown trend. Just slip any pair on and go. (Laces not included.)

John Lobb Lawry Chelsea Boots

Pair of dark brown slip-on boots. photo

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Fact: Every guy has, at some point, dreamt of being a cowboy. The sleek silhouette and sumptuous burnished leather on John Lobb's Lawry boots fulfill that fantasy; these Chelseas evoke a touch of life-on-the-edge mystery. Wear them with your best distressed denim for full effect. ($1,650; barneys.com)

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Suede Chelsea Boots by Common Projects

Light brown suede high-top slip-on boots. photo

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Every pair of Common Projects' iconic suede Chelseas come embroidered with a golden serial number, unique to each and every pair. It's one of those innocuous, near-negligible details that firmly plants this shoe into a class of its own. And that's without mentioning the luxurious suede, distinct rubber-crepe soles, or magical sand hue. (It somehow seems to match with everything. Seriously.) ($530; barneys.com)

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Stone Harness Chelsea by FRYE

Black leather harness chelsea boot. photo

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There's something about FRYE's leather—it's always a little distressed, a little lived-in—that we're head over heels for. And while it works on all of their shoes, their Stone Harness Chelseas, in all their rugged glory and Wild West attitude (that harness!), are the perfect match for the material. Giddy-up. ($358; thefryecompany.com)

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Polished Leather Chelseas by Saint Laurent

Polished leather slip-on boot. photo

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Saint Laurent perfected the Chelsea silhouette; slipping these boots on will automatically make you look slimmer and taller, and who doesn't want that? Pick up a pair in pristinely polished jet black leather. Wear them with your sharpest suit and you'll look like a billion bucks. (Yes, with a B.) ($945; ysl.com)

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Fleetwood Sharpei Chelsea by John Varvatos

Distressed chelsea boots. photo

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Sure, the Fleetwood Sharpei Chelseas, from John Varvatos, look like they've been run over, set on fire, and then washed in gasoline. But make no mistake—these suede boots are as luxurious as they come. The beat-up punk-rock mien is just all part of the appeal. Pair these with your best leather jacket and you'll look like you stepped straight out of the British Invasion. ($698; johnvarvatos.com)

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Chinchilla Boots by R.M. Williams

Light brown chinchilla boots. photo

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Check out the cascade of colors on the Chinchilla boots, by R.M. Williams. The slow descent from reddish brown to deep, sexy burgundy is evocative of an Australian Outback sunset—perfect, because that's where their shoes are crafted. (By hand, to boot.) ($645; rmwilliams.com)

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Curtis Boot by Allsaints

Sleek black leather boots with textured sides. photo

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Typically, Chelsea boots will have a mesh gusset. (That's the stretchy part.) But Allsaints has flipped convention on its head with their Curtis boot by designing a shoe with a leather one. These formal boots are unlike any Chelseas we've seen—and yes, they're just as elegant and cool as every other (more traditional) pair. ($308; allsaints.com)

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Liverpool Chelsea Dress Boot by Allen Edmonds

Light brown liverpool chelsea boots. photo

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If some lab scientists got together and created The Perfect Shoe, it would be the Liverpool Chelsea. The leather is wondrously supple, yes—but not so pristine that you'd be scared to wear them outside. The pointed shape combined with a soft rounded toe is a balancing act between too dandy and too casual. These work with everything, from a t-shirt to a tux. Get them in black, get them in walnut, or treat yourself—get both! ($445; allenedmonds.com)

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