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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Wine Red Leather Chukka Boots for Men
$339.99Wine red brings warmth and personality to the chukka boot's usually understated shape. The minimal eyelet lacing keeps the silhouette clean, and the color makes this a standout alternative to the more common brown or...
- SHOES
Brown Leather Chukka Boots for Men
$339.99The classic brown chukka boot, kept simple with minimal eyelets and no additional detailing. An easy, versatile choice that pairs with nearly anything from denim to lighter wool trousers.See our men’s Chukka boots styling guide,...
- SHOES
Black Leather Chukka Boots for Men, Classic
$339.99The black version of the classic chukka, formal enough to work with business-casual trousers while staying simple enough for everyday wear. A reliable boot for anyone who wants one dependable black option beyond a dress...
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Tan Croc-Embossed Captoe Chelsea Boots for Men
$360.99Croc-embossed leather adds texture to the clean Chelsea boot silhouette, and the captoe seam gives it a touch more structure than a plain-toe version. Tan keeps it versatile enough for both business-casual and weekend wear.See...
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Tan Leather Chukka Boots for Men, Classic
$336.99A lighter, warmer alternative to the black and brown chukka boots elsewhere in the collection. Tan works particularly well through spring and summer, pairing easily with lighter chinos or denim.See our men’s Chukka boots styling...
- SHOES
Black Leather Brogue Chelsea Boots for Men
$336.99Brogue perforations add texture to this Chelsea boot that a plain version doesn't have, while the elastic side panels keep the easy slip-on convenience Chelsea boots are known for. Black keeps it formal enough for...
- SHOES
Navy Leather Chelsea Boots for Men
$336.99A straightforward navy Chelsea boot without additional brogue or texture detailing — the color itself is the distinguishing feature here, offering a lighter alternative to black for business-casual settings.See our Chelsea boots styling guide, or...
- SHOES
Bronze Washed Leather Candy Ankle Boots for Men
$336.99The washed leather finish gives this boot a slightly distressed, matte texture rather than a polished shine, and the bronze color adds a metallic depth that flat brown doesn't have. A casual, everyday boot suited...
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Blue Suede Chelsea Boots for Men
$332.99The rubber sole makes this Chelsea boot more practical for daily wear than a leather-soled dress version, while the blue suede finish adds color and texture beyond the standard black or brown options. A comfortable,...
- SHOES
Wooden Brown Leather Chukka Boots for Men
$336.99A deeper, more muted brown than the standard tan chukka, "wooden" sits closer to a rich walnut tone. Works well for business-casual outfits that want something warmer than black without going as light as tan.See...
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Green & White Leather Cowboy Riding Boots for Men
$672.99A true western-style riding boot, distinct from the rest of the ankle boot collection in both shape and purpose. The green-and-white combination makes this a statement piece, built for horse riding or western-inspired outfits rather...
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Red Leather Cowboy Riding Boots for Men
$672.99The red version of the western riding boot, built with the same functional cowboy silhouette as the green-and-white pair above. A bold color choice for anyone wanting their western boots to stand out clearly from...
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Brown Alligator Leather Chelsea Boots for Men
$332.99The alligator-embossed texture gives this Chelsea boot more visual depth than a smooth-leather pair, while the classic elastic-side silhouette stays intact underneath. Brown keeps it versatile enough for both business and casual settings.See our Chelsea...
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Black Leather Jodhpur Boots for Men, Handmade
$329.99The strap-and-buckle detail is what defines a jodhpur boot, and this black version keeps that classic silhouette clean and versatile enough for business wear. Ankle-high and built in genuine leather, it sits comfortably under tailored...
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Brown Leather Elegant Chelsea Boots for Men, Handmade
$336.99A refined, polished take on the brown Chelsea boot without any additional exotic texture or brogue detailing — just clean leather and the classic silhouette. A dependable choice for business-casual settings.See our Chelsea boots styling...
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Burgundy Patina Leather Chelsea Boots for Men
$332.99The hand-painted patina finish gives this Chelsea boot more depth than a flat burgundy dye, warm and distinctive enough to stand apart from the more common black and brown versions elsewhere in the collection.See our...
