Chelsea Boots have been around since the Victorian Era, but it was the mod scene in 1960s England that really popularized the style (and guaranteed that the name “Chelsea” would be permanently attached to it).
Why should you care about any of this? We’ll tell you why. Aside from making you look a bit like style icons and respected rockers such as Bowie, Jagger, and Lennon, these classic, no-frills boots will never go out of style. Another bonus? They look just as good with a suit as they will with a pair of jeans. If you’re the type of guy that hates having too many different pairs of shoes for different occasions, you’ve met your match. Check out 15 of our favorites.
H&M Leather Chelsea Boots
If you’re trying your hand (or, perhaps more appropriately, your feet) at Chelsea boots for the first time, these boots from H&M are a good bet. Clocking in at just under $100, they sport the classic Chelsea boot style, are made out of buttery, slightly burnished leather, and will look great with everything from your jeans to your navy suit.
Bellfield Suede Chelsea Boots
Bellfield’s entire catalog borrows its style from the style of old school British explorers, but these midnight blue suede Chelsea boots are more rock n’ roll than mountain climber. The midnight blue coloring makes them cool without being garish, and opting for suede rather than leather makes you automatically more interesting, if not daring (just don’t wear these even if there’s a minor threat of rain).
Meermin Rapello Suede Chelsea Boots
Based in Mallorca, Meermin was established in 2001 by fourth generation craftsmen dedicated to making quality footwear for affordable prices. They accomplish that an more with these gorgeous Rapello suede Chelsea boots. Spray ‘em with a water repellant treatment and wear them with everything—with jeans to brunch or with a suit on Mondays.
Cole Haan Warren Chelsea Boots
Cole Haan specializes in making work-appropriate gear for the modern man, so it’s no surprise they have these Warren Chelsea boots on offer. Available in black or brown, these will serve as a respite from your regular work shoes, while still looking sharp. Crafted out of quality leather, they’re fully-treated to be waterproof, and have some serious tread on the bottom, so you can wear them in inclement weather without a care in the world (aside from wondering where the hell you put your umbrella).
Pete Sorensen Ankle Boots
Parisian brand Pete Sorensen’s shoes bend a little toward the metrosexual side, so if you can endure the cracks about wearing Marco Rubio’s boots, then these are for you. Women will love them.
Ted Baker Camroon Suede Chelsea Boots
Founded in the UK in the late 1980s, Ted Baker’s specialty was originally designing men’s dress shirts, but the brand has since expanded to include accessories, including high-quality footwear like these Camroon suede Chelsea boots. Luxe brown suede is broken up by navy blue, paisley-printed elastics to help you slip ‘em on, and more importantly, slip ‘em off after a long day.
Diemme Verona Boots
Inspired by hunting and mountain boots, these Verona boots from Italian footwear manufacturer Calzaturificio Diemme, are a blend of what you love about your rugged outdoor boots and what you need in a professional dress shoe. Crafted out of premium leather, the boots are a little taller than regular Chelsea boots and sport a white Vibram rubber sole, both intended to help you trudge through nasty weather without looking like a mountain man.
PS By Paul Smith Leather Chelsea Boots
From legendary British designer Paul Smith comes these leather Chelsea boots, which were crafted in Italy from premium leather and shined to maximum shininess. The shoe sports a classic design, but—as is typical in Paul Smith creations—there’s a bit of whimsy to it. The elastic gusset is black on the side that faces outward, but the interior one is kelly green, adding a subtle pop of color that they’ll have to look twice for to notice.
Frye James Chelsea Boots
Massachusetts-based Frye has been making high-quality boots and leather goods since 1863, when its namesake, John A. Frye opened the doors to his first shop in Marlboro. Their commitment to making quality, no-frills pieces that will last forever is evident in everything they make, least of which the James Chelsea boots. Crafted out of Italian leather, the boots are available in brown with elastic gussets, or in all-black if you want to look extra rock ‘n’ roll.
Grenson Jacob Chelsea Boots
UK-based Grenson has been creating quality footwear since the 19th century, and these Chelsea Boots are no exception. Made from high-quality leather (and featuring Grenson’s signature punched brogue detailing), they feature elasticated side panels and a canvas heel pull, which will make it easy to kick ‘em off and put ‘em on. Who has time to spend with laces anyway?
A.P.C. Suede Chelsea Boots
French brand A.P.C. stands for “Atelier de Production et de Création,” which roughly translates to “workshop of production and creation.” A.P.C. has been producing/creating quality wares since it was founded in Paris in the late 1980s, and these luxe suede Chelsea boots show they’ve still got it 30 years later. Made out of tan suede and featuring sturdy rubber soles, they ape the look of a classic work boot but look a helluva lot more sophisticated.
Common Projects Suede Chelsea Boots
NYC-based Common Projects has become a hot commodity among the urban fashion set since it was founded in 2004, and in looking at these suede Chelsea boots, it’s easy to see why. Made in Italy, these boots (available in gray or beige), feature a crepe rubber sole (popular on classic chukka boots) and the ankle stamped with the brand’s signature numerals.
Church’s Houston Leather Chelsea Boots
When you buy a pair of kicks from UK-based Church’s, you know you’re getting the real deal (the brand has shoemaking roots stretching all the way back to 1675), so while they’re expensive, you can justify the splurge. These all-black Chelsea boots are also all-business, and will quickly replace your oxfords as your favored suit companion.
Edward Green Camden Suede Chelsea Boots
Speaking of splurges, let us introduce you to your next one—these Camden suede Chelsea boots from Edward Green, which was founded in England in the late 1800s. Made from high-quality materials, these shoes just look expensive, even from far away, which is probably what you’re going for when you shell out over a grand for something you wear on your feet.
Berluti Burnished Leather Chelsea Boots
And hey, if you won the Powerball last week, we highly recommend snatching up a pair of these Burnished leather Chelsea boots from legendary Italian brand, Berluti. Made from their signature Venezia leather, the shoes have a beautiful patina right out of the box. These are shoes that are guaranteed to earn you compliments—from everyone—wherever you go.
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