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.
- variable
Brown Leather Calf-High Military Boots for Men
$359.99Taller than the standard ankle boots in this collection, the calf-high shaft gives more coverage and a more rugged, utilitarian look. Brown leather and military-inspired styling make this a durable option for outdoor or cold-weather...
- variable
Brown Leather Cap Toe Dress Boots for Men
$363.99The cap toe seam is a small detail that adds structure and formality to this boot, making it a strong match for suit trousers in a way a plain-toe boot can't quite achieve. Brown leather...
- variable
Brown Leather Double Buckle Military Boots for Men
$419.99This is the only boot in the Buckles collection, and it leans utilitarian — the military-inspired shape and double buckle closure (instead of laces or a zip) make it faster to put on and take...
- variable
Brown Leather Wingtip Chelsea Boots for Men
$345.99Wingtip brogue detailing on a Chelsea boot is a less common combination than the usual plain toe, giving this pair more visual interest while keeping the clean, elastic-side silhouette that makes Chelsea boots so versatile....
- variable
Brown Patina Leather Ankle Boots for Men
$320.99The hand-painted patina finish gives this boot more depth and tonal variation than a flat brown dye — it looks less uniform and more like a boot with some history to it, right out of...
- variable
Brown Patina Military-Style Ankle Boots for Men
$332.99This pairs the military boot's sturdier, more utilitarian shape with the tonal depth of a hand-painted patina finish — a boot that's built for durability but still has some visual richness to the leather rather...
- variable
Brown Patina Wingtip Ankle Boots for Men
$329.99Wingtip brogue detailing across the toe adds texture and visual interest that a plain-toe boot doesn't have, and the hand-painted patina finish deepens the brown tone further. A strong choice for business-casual settings where you...
- variable
Brown Patina Leather Chelsea Boots for Men
$345.99The hand-painted patina finish gives this Chelsea boot more depth than a flat brown dye, while the classic elastic-side silhouette keeps it easy to wear and versatile across business-casual and weekend outfits.See our Chelsea boots...
- variable
Brown Patina Double Monk Dress Boots for Men
$335.99Combining a boot's taller shaft with a double monk strap buckle closure gives this pair more formal structure than a standard ankle boot. The hand-painted patina finish adds tonal depth, making this a strong choice...
- variable
Wingtip Brown Patina Ankle Boots for Men
$333.99Wingtip brogue detailing across the toe adds texture and visual interest that a plain-toe boot doesn't have, and the hand-painted patina finish deepens the brown tone further. A strong choice for business-casual settings where you...
- variable
Brown Suede Ankle Boots for Men
$320.99A straightforward brown suede ankle boot without additional detailing like wingtips or brogue — the simplicity is the point here, making it one of the easiest boots in the collection to pair with almost anything...
- variable
Brown Suede Dress Boots for Men
$320.99This version takes the same brown suede finish into slightly more formal territory, built with a cleaner, dressier silhouette suited to business-casual offices rather than purely casual wear. The suede texture keeps it from looking...
- variable
Brown Suede Wingtip Ankle Boots for Men
$320.99Wingtip brogue detailing on a suede boot is a less common combination than on smooth leather, giving this pair more texture and visual interest while staying in smart-casual territory rather than strict business formal.Compare materials...
- variable
Men’s Brown Suede Dress Boots
$324.99A refined brown suede boot built for slightly more formal settings than an everyday chukka or ankle boot, while the suede texture keeps it from looking as stiff as a full leather dress boot.Compare materials...
- SHOES
Black Washed Leather Candy Chelsea Boots for Men
$336.99The washed leather finish gives this Chelsea boot a slightly distressed, matte texture rather than the usual polished shine — more casual and rugged than a standard dress Chelsea, suited to daily wear.See our Chelsea...
- SHOES
Dark Blue Washed Leather Candy Chelsea Boots for Men
$336.99The dark blue version of the washed-leather Chelsea boot, with the same distressed matte texture as the black option in a cooler, more distinctive tone. Good for casual outfits where a polished dress boot would...
