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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Dark Brown Leather Ankle Boots for Men, Classic
$336.99Dark brown sits closer to black in formality than the standard brown ankle boot, making this a strong choice for business settings that want to avoid black without going too casual. Clean, classic shape with...
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Light Brown Leather Ankle Boots for Men, Classic
$336.99A lighter, warmer alternative to the dark brown version above, well suited to spring and summer smart-casual outfits. Same clean, classic ankle boot shape without additional styling details.Read our brown leather boots guide, or browse...
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Brown Patina Leather Jodhpur Boots for Men, Handmade
$329.99The strap-and-buckle detail keeps the classic jodhpur silhouette intact, while the hand-painted patina finish gives the brown tone more depth than a flat dye. A versatile boot for both business-casual and smart-casual settings.Read our brown...
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Blue Patina Leather Wingtip Boots for Men, Handmade
$329.99The hand-painted patina finish gives this blue wingtip boot more depth than a flat dye, while the color itself sets it apart from the black and brown boots that dominate most collections. A confident choice...
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Brown Leather Chukka Boots for Men, Handmade
$332.99Chukka boots are built around simplicity — minimal eyelets, a clean unadorned upper, no cap toe or brogue detailing to distract from the shape. This brown pair keeps that same understated design, making it one...
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Brown Leather Ankle Boots for Men, Classic Handmade
$332.99A dependable, no-frills brown ankle boot without any chukka, Chelsea, or brogue-specific styling — just a clean classic shape that works across most smart-casual and business-casual outfits.Read our brown leather boots guide, or browse the...
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Genuine Leather Army Boots for Men, Handmade
$419.99Built with a sturdier, more utilitarian shape than the dress or Chelsea boots elsewhere in the collection, this army-style boot is meant for durability over polish. A practical choice for anyone who needs a boot...
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Grey Leather Wingtip Boots for Men, Handmade
$320.99Grey is a genuinely uncommon color for a wingtip boot, giving this pair a modern, distinctive look next to the more common black and brown options. Formal enough for business wear while standing out clearly...
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Tan Brown Leather Jodhpur Boots for Men, Handmade
$327.99A warmer alternative to the black and brown patina jodhpur boots elsewhere in the collection, this tan version keeps the classic strap-and-buckle closure while staying light enough for spring and summer wear. Versatile for both...
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Tan Brown Ostrich Leather Boots for Men
$345.99The raised quill pattern of ostrich leather gives this boot a texture that no smooth calfskin pair can replicate. In tan brown, it stays wearable for daytime and business-casual settings rather than reading as purely...
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Tri Tone Genuine Leather Boots for Men, Handmade
$320.99Three leather tones combined on one boot make this a genuine statement piece, distinct from the more common single or two-tone options in the collection. Best paired with simple, solid-color outfits that let the boot...
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Chocolate Brown Leather Ankle Boots with Zip for Men
$336.99The side zip closure makes this boot faster to put on than a lace-up equivalent, without sacrificing the clean silhouette a formal ankle boot needs. Chocolate brown keeps it warm and versatile, well suited to...
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Black Washed Leather Medium Diver Boots for Men
$336.99This medium-height diver boot sits between an ankle boot and the taller "high diver" version elsewhere in the collection, keeping the same rugged, weather-ready sole in a shorter shaft. The washed leather finish adds a...
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Dark Brown Washed Leather Medium Diver Boots for Men
$336.99The dark brown version of the medium diver boot, with the same durable sole and washed leather texture as the black option, shifted into a warmer tone that pairs easily with denim or heavier casual...
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Tan Washed Leather Medium Diver Boots for Men
$336.99The lightest of the three medium diver colorways, this tan version keeps the same rugged sole construction while offering a more casual, warm-weather-friendly tone than the black or dark brown options.Learn what to look for...
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Dark Brown Suede Ankle Boots for Men
$344.99A straightforward dark brown suede ankle boot without additional styling like wingtips or jodhpur straps — the deep tone and soft texture are the focus, making it a versatile addition to a smart-casual wardrobe.Compare materials...
