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Chic Winter Booties
(Photo: Shutterstock)

9 Chic Booties Perfect for Winter Travel

Dressing for winter shouldn’t mean giving up style in the name of warmth and comfort. From head to toe, travel-friendly winter gear can keep you looking sharp in the chilliest conditions. Ankle booties in particular are a secret weapon for chic travelers.

Chic Booties for Women Perfect for This Winter

For winter travel, boots are a must. Not only do they warm and protect, they add sure-footed style to any outfit. But they can also add bulk and weight to a suitcase. Happily, ankle booties are there to save the day. Here are 10 easy-to-pack, super-chic booties for women just waiting to accompany you on your next winter jaunt.

Charleston Telfair Boots

Charleston telfair boots
(Photo: Charleston Shoe Co.)

The elegant Telfair Boot from Charleston Shoe Co. delivers good height without sacrificing walkability. The stacked two-inch heel gets high marks for comfort and looks dressy enough to wear out at night. This adaptable ankle boot comes in 10 different colors and patterns, and since it’s machine washable (really), winter mud and dirt won’t slow you down.

Merrell Women’s Chateau Mid Pull Waterproof Booties

Merrell women’s chateau mid pull waterproof booties
(Photo: Amazon)

Wet weather is no match for the Women’s Chateau Mid Pull Waterproof booties from Merrell. The full-grain leather and impermeable textile uppers seal out water while letting moisture (read: sweat) escape. Durable outsoles offer serious grip on slippery surfaces, and the super-comfortable contoured EVA footbed helps control odors. The 1.9-inch heel adds height and style but is still comfortable enough to not slow you down even if you’re walking all day.

Clarks Maypearl Ramie Ankle Booties

Clarks maypearl ramie ankle booties
(Photo: Amazon)

The Maypearl Ramie Ankle Bootie, part of the Clarks artisan collection, is a stacked-heel bootie with a streamlined look. Easy to pull on and off thanks to an unobtrusive zipper, the ankle boot comes with a built-in leather sock liner and impact-absorbing OrthoLite bootbed for added comfort. Choose among three leather color options—black, mahogany, and dark tan.


Dream Pairs CINQ Low Wedge Heel Ankle Boots

Dream pairs cinq low wedge heel ankle boots
(Photo: Amazon)

The ultra-affordable Dream Pairs Women’s CINQ Low Wedge Heel Ankle Boots offer cozy coverage and a faux-fur lining for winter walking. The low-wedge heel adds height but still feels stable, and six color options—including gray and red—keep your winter look fresh.

LONDON FOG Hester Warm Lined Booties

LONDON fog hester warm lined booties
(Photo: Amazon)

The LONDON FOG Women’s Hester Warm Lined Bootie is both fashion-forward and winter-friendly—the perfect combination for winter travelers. These two-inch-heeled ankle boots are lined for added warmth and have faux-fur detailing for style and to prevent chilly drafts. They’re comfortable but not clunky, and the soles have sturdy tread to reduce slips.

TOMS Leila Boots

TOMS leila boots
(Photo: Amazon)

The Leila Boot offers the comfort you expect from TOMS in a winter-friendly bootie format. These stacked-heel ankle boots have a comfort insole, a rubber sole, and a tassled back zipper. Best of all, they come in more than 20 colors/pattern combinations featuring leather, wool, and textile uppers.

Lucky Brand Basel Boots

Lucky brand basel boots
(Photo: Amazon)

The Lucky Brand Women’s Basel Boot is a low-heeled leather bootie with zippers on both sides and a pull tab at the back. The stacked 1.5-inch heel and round-toe construction boosts the comfort quotient, and you’ll find the bootie’s chic silhouette in more than two dozen colors and patterns.

Birkenstock Stowe Leather Boots

Birkenstock stowe leather boots
(Photo: Amazon)

Indulge in the famed comfort of Birkenstock with these Stowe Leather Boots. With their one-inch heel and slightly higher boot shaft, these booties look more like low boots than true ankle boots. They offer the German sandal company’s super-comfortable footbed plus cool details like an adjustable buckle and side zipper.

Aerosoles Push N Pull Boots

Aerosoles push n pull boots
(Photo: Amazon)

Get a classic Chelsea boot with a comfort boost in the Push N Pull Boot from Aerosoles. Diamond-flex soles and a memory foam insole increase all-day comfort, while beautiful leather, a one-inch heel, and double-elastic gores complete the look.

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