The 20 best ankle boots for men in 2023 (2024)

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New Republic Sonoma Suede Chelsea Boot

New Republic's Sonoma suede Chelsea boot can go toe-to-toe with much pricier brands thanks to its high-quality materials and construction, and impeccable style.

New Republic is a direct-to-consumer footwear brand that produces incredibly stylish, well-made boots that can go toe-to-toe with high-end brands and not drain your wallet. The Sonoma suede Chelsea boot is extremely comfortable straight out of the box, features a beautiful suede upper, is lined in leather, and has a natural crepe sole that's springy and supportive. No wonder The Sonoma is one of the brand's bestsellers.

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Florsheim Norwalk Zip Up Boot

Classic looks and comfort make these boots from the American heritage brand perfect for everyday wear.

Florsheim's Norwalk Zip Up Boots have looks and comfort in equal measure. These boots from the American heritage brand have handsome leather uppers and a traditional side zipper, while inside, they incorporate technology designed to keep your feet happy for all-day wear. They feature springy foam insoles and soft yet resilient midsoles — like you'd find in running shoes — and flexible outsoles, all at a reasonable price. They're likely to become your everyday ankle boots.

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Milwaukee Boot Company Lakefront Boot

Milwaukee Boot Company's Lakefront boots are the brand's "no-frills chukka" that are perfect for day-to-day wear thanks to straight-out-of-the-box comfort and rugged good looks.

Milwaukee Boot Company is a newer brand launched by the folks behind Moral Code, a DTC footwear brand we love for both its products and ethical stance. The Lakefront boot is the Milwaukee Boot Company's "no-frills chukka" and has become one of my everyday boots, thanks to its straight-out-of-the-box comfort and rugged good looks. These pair well with all my fall favorites — cords, cardigans, chore coats, and Western fedoras.

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Frye Paul Inside Zip Boot

Frye, an American heritage brand, goes all out with the Paul Inside Zip Boot. Hand-burnished leather uppers, antiqued hardware, and Goodyear welting make for one elegant boot.

Frye is a heritage boot brand that continues to produce outstanding footwear. The Paul is simply beautiful with its hand-burnished pull-up leather uppers, antiqued hardware, and Goodyear welting that allows for a cobbler to replace the outsole when the time comes.

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Blundstone Men's Classic Chelsea Boot in Green

You can't have an ankle boot roundup without Blundstone. Their classic Chelsea boots in dark green are both tough and stylish.

You can't have an ankle boot story without Blundstone. The Australian heritage brand (still family-owned more than 150 years on) is the epitome of the hard-wearing Chelsea boot style beloved by everyone from farmers to fashion editors. This version in a dark green combines the best of what makes the brand so beloved: toughness (waterproof premium leather upper, a durable thermoplastic polyurethane outsole) and style (bold color, iconic look).

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Mark Nolan Lincoln Boots

The vibrant Marc Nolan Lincoln boots made using top-notch materials and techniques that are anything but ordinary.

If you're looking for ankle boots that stand out from the crowd and come in at a reasonable price, Mark Nolan is the brand for you. The Lincoln Boots, especially the Rose Pink colorway, highlight what makes Mark Nolan so special. Besides the eye-catching color, these cap-toe boots feature top-quality Mohawk suede and soft calf leather lining, Blake stitching for flexibility and easy resoling down the line, and leather outsoles with traction inserts. The other colorways are equally captivating, from a rich brown snakeskin to a bright white calf leather, each of these boots are a standout.

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La Canadienne Luca Boot

La Canadienne's Luca Boot is rugged yet refined and crafted in Italy from a gorgeous waterproof nubuck suede.

Montreal based-brand La Canadienne has recently ventured into men's footwear, and are clearly off to a strong start. The company combines style, sustainability, quality, and comfort in its products that are all either made in Canada, Italy, or Spain. They handcraft the Luca Boot from a waterproof Italian nubuck suede in Italy and line it in breathable leather. The look is rugged, thanks to its lug sole, but with a refined nubuck upper, to get you from a business casual workplace to a weekend spent outdoors.

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Clarks Wallabee Boot

Clarks Wallabee Boots have a distinctive silhouette and several unique colorways. These are great statement boots that you'll never want to take off.

Clarks Wallabee boots are as distinctive as the work of hip-hop legends Wu-Tang Clan, who loved these boots so much they rapped about them. The Wallabee, which is somewhere between a moccasin and a chukka, and is as comfortable as the former and as sturdy as the latter, comes in several colorways as unique as the silhouette, including lime. These should be your fall statement boots.

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Unmarked French Toe Chelsea

The Unmarked French Toe Chelsea is a supremely elegant boot that's handmade in León, the heart of Mexico's renowned bootmaking industry, and has everything you'd want in an ankle boot.

Unmarked is a footwear company that perfectly combines traditional boot-making techniques with contemporary style and a sustainable approach. The French Toe Chelsea is a supremely elegant boot with a squared-off toe, beautiful leather uppers made in an environmentally friendly manner, and Goodyear welting. These handmade boots are manufactured in León, the heart of Mexico's renowned boot-making industry, in a workshop that pays its workers fair wages.

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Hush Puppies Detroit Chukka

Hush Puppies Detroit Chukkas are comfortable and casually cool and water resistant, in case you get caught in the rain.

Hush Puppies is known for its casual, comfortable footwear and the Detroit Chukka has both in spades, along with a dose of cool. These boots will pair with all your fall looks, whether it's a sport coat and chinos or jeans and a leather jacket. They come in both full-grain leather and a soft suede, and are water-resistant.

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Astorflex Bitflex Chelsea

The Astorflex Bitflex Chelsea is a sophisticated boot that's handmade in Italy using eco-friendly European leather and comes at a great price for what you get.

The Bitflex Chelsea boot is handmade in Italy by Astorflex — a multi-generational family footwear company — using eco-friendly European leather. These boots are not only well made and sophisticated with leather outsoles and stacked heels, they're also comfortable thanks to ergonomic footbeds. They're also nicely priced for what you get.

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Thursday Boots Rogue Jodhpur Boot

The Thursday Boots Rogueis a Jodphur boot that's urbane yet tough, built to last, and priced right.

Thursday Boots, one of our favorite DTC boot companies, offers the Rogue, a Jodphur boot that's built to last, thanks to manufacturing techniques like Goodyear welting. It comes in at under $200. The dark olive suede is a particular standout. And like all the company's boots, they're comfortable thanks to glove leather interiors, cork-bed midsoles, and shock-absorbing insoles.

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Beckett Simonon Laval Chukka

Beckett Simonon's Laval chukkas are a classic handmade in Colombia using full-grain Italian calfskin and Blake stitching for years of wear.

Beckett Simonon, another DTC footwear brand, uses a made-to-order model for their boots that are handmade by artisans in Colombia. The Laval chukka is made from Italian full-grain calfskin that's supple yet resilient, and will only get better with age. These boots are a true classic that will dress up whatever you pair them with and thanks to their Blake stitching, which (like Goodyear welting) means they can be resoled, and you'll get years of wear out of them.

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Taylor Stitch Trench Boot

Don't be fooled by the good looks of the Taylor Stitch Trench Boots. Yes, they have a buttery soft sheepskin lining and antique brass hardware, but these boots are made to take whatever you throw at them.

The Taylor Stitch Trench boot takes a utilitarian style first used by soldiers during World War I and punches it up with a handmade version, incorporating a soft sheepskin lining, Goodyear welting, a Vibram outsole, and antique brass hardware. But don't be fooled by their good looks. These boots are built to take whatever you throw at them. Like some of the other selections in this roundup, the Taylor Stitch trench boots are made in León, Mexico.

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Tecovas The Chance Western Chelsea

The Chance, by the digital-first Western wear brand Tecovas, is a Chelsea boot with some cowboy swagger. It features calfskin uppers, a leather outsole and stacked heel, and Goodyear welting.

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To Boot New York Providence Jodhpurs

To Boot New York's Providence boots aren't your ordinary Jodhpurs. The boots are made in Italy of full-grain calfskin and will dress up everything you wear with them.

To Boot New York's Providence bootsare not your everyday Jodhpurs. These luxe boots are made in Italy of full-grain calfskin, and feature a polished silver buckle on the strap that helps secure them, as well as a side zipper. They're Blake stitched (which means they can be resoled), are lined in leather, and have a cushioned leather-covered insole. These Jodhpurs will add panache to whatever you pair them with.

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Clae Gibson

The Clae Gibson is a boot that wears like a sneaker, for a perfect combination of style and comfort.

The Los Angeles-based footwear brand Clae has mastered sustainability produced minimalist footwear over its two decades as an independent producer. The Gibson is a minimalist boot that wears like a sneaker. It features a premium leather upper on a cushiony rubber outsole, and comes in three colorways, including a striking walrus brown.

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Taft Dylan Boot in Woven

The Taft Dylan Boot in Wovenis a stunning interpretation of the Jodhpur boot that's handcrafted in Spain by this DTC company known for unique versions of classic silhouettes.

The Taft Dylan boot is another unique interpretation of the Jodhpur boot from the DTC brand that's unparalleled in creating extraordinary iterations of dress boots and shoes using old-world techniques and high-end materials. There are four styles of the Dylan boot, but we're highlighting the woven version; it's not only unique but extremely attractive. The leather is handwoven in Spain and then burnished by hand using heat and different stains for a gorgeous finish. It's Blake stitched, so it can be resoled down the line.

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Grant Stone Chelsea Boot in Crimson Chromexcel

The Grant Stone Chelsea boot is a stellar example of the style that combines beauty and brawn, for boots that will continue to wow you for years to come.

The Grant Stone Chelsea combines beauty and brawn in one package. The uppers are made from Chromexcel leather at Horween — one of the oldest tanneries in the United States — that's supple but strong, deeply hued and will only get better with age. The boots are Goodyear welted, and have a leather lining, insole, welt, and midsole. Because Grant Stone is a DTC brand, you get a lot of luxury for a fair price.

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Baabuk Sky Wooler Black Edition

The Baabuk Sky Wooler Black Edition is somewhere between a hightop and a boot that's made from Portuguese mulesing-free sheep wool and topgrain nubuck, and is perfect for fall.

We sometimes like to throw in an outlier in our roundups, and the Baabuk Sky Wooler Black Edition fits the bill. Somewhere between a high-top and a boot, the uppers are made from Portuguese mulesing-free sheep's wool that's water-resistant and extra thick for colder fall nights. The Sky Wooler, which is designed in Switzerland and produced in Portugal, has topgrain nubuck at the tongue, ankle, and heel counter and is easy to get in and out of thanks to the no-tie elastic laces. These minimalist beauties are super comfortable and look smart when paired with chinos and a cardigan, but also work with jeans and a henley.