Men's Ankle Boots (107)
Chelsea, Chukka, Jodhpur & Dress Boots
Shop ankle boots for men in Chelsea, chukka, jodhpur, and dress styles, crafted in leather and suede for everyday wear. Designed for comfort, versatility, and a polished look, these men’s ankle boots pair easily with denim, trousers, and season-to-season outfits. Explore black ankle boots, brown ankle boots, and soft suede options from Marcello Sarto and Marchello Shoes.
Need styling ideas? Read our Chelsea boots styling guide, or compare dressier options in our men’s Oxford & wingtip shoes.
Looking for a more focused edit? Browse our taller ankle boot styles.
Choosing between boot styles? See our Chelsea boots buying guide and our guide to black leather boots.
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Black Leather Amphibious Brogue Boots for Men
$336.99"Amphibious" styling means a chunkier, more durable sole than a standard dress boot, built to handle wet or rough conditions without sacrificing the brogue detailing on the upper. In black leather, it strikes a balance...
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Tan Leather Amphibious Brogue Boots for Men
$336.99The tan version of the amphibious brogue boot keeps the same durable, weather-ready sole construction while shifting to a warmer, more casual color. Good for outdoor wear or unpredictable weather where a standard dress boot's...
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Black Washed Leather Diver Boots for Men
$336.99The washed leather finish gives this boot a slightly distressed, matte texture rather than a polished shine — more rugged and less formal than a standard dress boot. Built with a "diver" style sole for...
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Tan Washed Leather Diver Boots for Men
$336.99The tan colorway of the diver boot keeps the same rugged, washed-leather texture and durable sole, shifted into a warmer tone that pairs naturally with denim or heavier casual trousers. Built for practicality over polish.Learn...
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Dark Brown Washed Leather Diver Boots for Men
$336.99The dark brown option in this diver boot line sits between the black and tan versions — dark enough to still read as fairly versatile, while keeping the same textured, washed leather finish and heavy-duty...
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Beige Leather Lace-Up Ankle Boots for Men
$336.99Beige is a lighter, warm-weather-friendly alternative to the darker leather ankle boots elsewhere in the collection. The classic lace-up closure keeps the shape structured, well suited to spring and summer smart-casual outfits.Learn what to look...
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Dark Brown Leather Lace-Up Ankle Boots for Men
$336.99A dependable dark brown lace-up ankle boot, formal enough for business-casual wear while staying versatile for everyday use. No additional detailing beyond the classic lace-up closure and clean silhouette.Read our brown leather boots guide, or...
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Ox-Blood Leather Chelsea Boots for Men
$345.99Ox-blood is a deeper, richer alternative to standard brown or burgundy — dark enough to work in formal settings, distinctive enough to stand out from the far more common black or brown Chelsea boot. The...
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Red Patina Leather Military Boots for Men
$336.99Red is a genuine statement color for a boot, and the hand-painted patina finish adds tonal depth on top of that boldness. Built with the sturdier military-style construction found elsewhere in the collection, this is...
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Sky Blue Leather Double Monk Boots for Men
$320.99Sky blue is a rare, eye-catching color for a boot, and pairing it with a double monk strap buckle closure makes this one of the more detailed, distinctive pieces in the whole collection. Best worn...
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Tan Brown Leather Wingtip Ankle Boots for Men
$329.99A warmer, more casual take on the wingtip ankle boot than the black or dark brown versions elsewhere in the collection. The brogue detailing across the toe adds texture, and tan brown keeps it wearable...
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Tan Ostrich Leather Boots with Zipper for Men
$345.99The zip closure makes this boot faster to put on than a lace-up equivalent, while the ostrich leather texture keeps it visually distinctive next to a shelf of smooth-leather boots. Tan keeps the overall look...
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Black Chelsea Boots for Men, Handmade Leather
$339.99Chelsea boots earn their place in a wardrobe by doing more than any other boot — this black pair works under suit trousers for the office just as easily as it does with raw denim...
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Brown Leather Chelsea Boots for Men
$339.99A reliable brown Chelsea boot without any additional brogue or exotic-texture detailing — clean leather and the classic elastic-side design, versatile enough to wear under suit trousers or with denim.See our Chelsea boots styling guide,...
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Grey Leather Chelsea Boots for Men
$336.99Grey gives this Chelsea boot a cooler, more modern look than the standard black, brown, or navy options elsewhere in the collection. The classic elastic-side silhouette stays easy to wear across business-casual and weekend outfits.See...
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Brown & Blue Cross Strap Boots for Men
$336.99The cross strap detail sets this boot apart from the standard lace-up, zip, or elastic-side closures found elsewhere in the collection, and the brown-and-blue two-tone finish adds further visual interest. A genuinely distinctive piece for...
