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
Dark Tan Washed Leather Candy Chelsea Boots for Men
$336.99The dark tan colorway rounds out the washed-leather Chelsea boot line, offering a warmer alternative to the black and dark blue versions. Casual and rugged in texture, suited to daily wear rather than formal occasions.See...
- SHOES
Black Leather Chelsea Boots for Men
$336.99A dependable black Chelsea boot without brogue detailing or a washed texture — smooth leather and the classic elastic-side design, versatile enough to work under suit trousers or with denim.See our Chelsea boots styling guide,...
- SHOES
Brown Leather Brogue Chelsea Boots for Men
$336.99Brogue perforations add texture to this brown Chelsea boot that the plain version doesn't have, while the elastic side panels keep the easy slip-on convenience intact. A strong alternative to the black brogue Chelsea boot...
- SHOES
Black Washed Leather Chelsea Diver Boots for Men
$336.99This blends the Chelsea boot's easy elastic-side silhouette with the diver boot's more rugged, durable sole — practical for daily wear in a way a standard dress Chelsea isn't. The washed leather finish adds a...
- SHOES
Dark Brown Washed Leather Chelsea Diver Boots for Men
$336.99The dark brown version of the Chelsea diver boot, keeping the same durable sole and washed texture as the black option in a warmer, slightly more versatile tone.See our Chelsea boots styling guide, or browse...
- SHOES
Tan Washed Leather Chelsea Diver Boots for Men
$336.99The lightest of the Chelsea diver colorways, this tan version pairs the rugged, durable sole construction with a warm-weather-friendly tone suited to casual, everyday wear.See our Chelsea boots styling guide, or browse the full men’s...
- variable
Dark Brown Alligator Texture Leather Boots for Men
$324.99The alligator-embossed texture gives this boot more visual depth than a smooth leather pair, while dark brown keeps it grounded enough for regular business-casual wear. A strong option for anyone who wants an exotic-leather look...
- variable
Dual Tone Brown Wingtip Ankle Boots for Men
$320.99Two shades of brown leather combined with wingtip brogue detailing give this boot more depth and visual interest than a single-tone pair. A strong option for anyone who wants their boots to carry some personality...
- SHOES
Vintage Black Leather Ankle Boots for Men
$336.99A classic black ankle boot with a "vintage" construction that gives it a slightly more traditional shape than the more modern chukka or Chelsea styles elsewhere in the collection. Versatile enough for both business-casual and...
- variable
Forest Green Suede Chukka Boots for Men
$320.99Forest green is a genuinely uncommon color for a chukka boot, giving this pair an earthy, distinctive tone that stands apart from the usual tan, brown, and black options. The minimal eyelet lacing keeps the...
- variable
Green Leather Long Boots for Men
$336.99Taller than the standard ankle boots in the collection, this long boot uses a bold green leather to make a clear style statement. Best suited to someone confident wearing color as a central part of...
- variable
Green & Black Suede Wingtip Chukka Boots for Men
$345.99Green paired with black suede gives this chukka boot an earthy, unusual color combination not typically seen in formal footwear, while the wingtip brogue detailing adds texture beyond the usual minimalist chukka shape. A distinctive...
- variable
Grey & Black Suede Wingtip Boots for Men
$348.99Grey and black suede together give this wingtip boot a cooler, more modern color palette than the brown-toned boots elsewhere in the collection. The suede texture and brogue detailing add depth, making this a distinctive...
- variable
Grey Patina Suede Button Boots for Men
$320.99The button closure is a less common detail than laces or a zip, giving this grey suede boot a slightly vintage character. The hand-painted patina finish adds tonal depth, making this a distinctive choice for...
- variable
Grey Suede Jodhpur Boots for Men
$351.99Grey is a rarer color choice for a jodhpur boot, giving this pair a distinctly modern look compared to the standard black or brown versions. The suede finish keeps it casual enough for everyday wear,...
- variable
Tri Tone Wingtip Ankle Boots for Men, Handmade
$329.99Three leather tones on one boot is a bolder move than the two-tone options elsewhere in the collection — this is a boot built to be the focal point of an outfit rather than blend...
