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.
- SHOES
Black Full Grain Leather Ankle Boots for Men
$344.99Full-grain leather is the highest-quality hide available, and this black ankle boot keeps the finish smooth and polished for business or formal settings. No additional detailing here — just quality material and a clean, dependable...
- SHOES
Brown Full Grain Leather Ankle Boots for Men
$344.99The brown counterpart to the black full-grain ankle boot, offering the same high-quality leather and smooth finish in a warmer, slightly more casual tone. Versatile enough for both business-casual and weekend wear.Read our brown leather...
- SHOES
Dark Blue Suede Ankle Boots for Men
$344.99Dark blue suede offers a cooler, more distinctive alternative to the brown and black suede boots elsewhere in the collection. The smooth suede finish keeps it casual enough for everyday wear while still looking intentional...
- SHOES
Light Brown Leather Chelsea Boots for Men
$336.99A lighter, more casual alternative to the standard brown or black Chelsea boot, well suited to spring and summer outfits. The smooth leather finish and elastic side panels keep the easy, classic Chelsea silhouette intact.See...
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Tan Brown Patina Leather Equestrian Riding Boots for Men
$740.99Built specifically for horse riding rather than everyday city wear, this tall equestrian boot uses a hand-painted patina finish for extra depth in the tan brown leather. A functional choice for riding, or a distinctive...
- SHOES
Cognac Wingtip Chukka Boots for Men
$336.99Cognac brings warmth and richness to the chukka boot's simple silhouette, and the wingtip brogue detailing sets it apart from the plain chukka boots typically seen elsewhere. A versatile boot for smart-casual outfits, working well...
- SHOES
Olive Brown Wingtip Chukka Boots for Men
$339.99Olive brown is an uncommon color for a chukka boot, giving this pair an earthy, distinctive tone next to the more common tan and black options. The wingtip brogue detailing adds texture to what's normally...
- SHOES
Croc Brown Wingtip Lace Up Boots for Men
$336.99Croc-embossed leather gives this wingtip boot more texture than the smooth-leather tan version found elsewhere in the collection, and the brogue perforations add further detail across the toe. A boot for anyone who wants their...
- SHOES
Tan Wingtip Lace-Up Boots for Men
$336.99Wingtip detailing on a boot is a small thing that changes the whole silhouette — this tan pair uses hand-painted full-grain leather in a dual-tone finish, with brogue perforations across the toe that catch light...
- SHOES
Tan Leather Zipper Boots for Men
$336.99The zip closure makes this boot faster to put on than a lace-up equivalent, and tan keeps it light and versatile through warmer months. A practical, everyday option where convenience matters as much as style.Read...
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Brown Patina Leather Equestrian Riding Boots for Men
$740.99The darker brown counterpart to the tan equestrian riding boot, with the same hand-painted patina finish and tall shaft built for horse riding or an equestrian-inspired look.Learn what to look for in our handmade leather...
