The Best Ankle Boots


To sport your ankle-length jeans and cropped flares into the cold season, nothing looks better than a slick pair of booties. Breaking the silhouette just above the bone, the ankle boot elongates the leg and adds a brisk nonchalance. From rugged to refined, ankle boots come in all shapes and colors to style all your favorite outfits of the season.

Cat Footwear has plenty of rugged versatile booties to choose from. The industrial inspired line, which is made out of premium leather, has whimsical touches on new models that give them a one of the kind appeal. This cool pair of Olive boots with its full grain stained leather and crafted nail embellishments is my favorite. The back laces feminize the tough edge of the boot without sacrificing the excellent Cat’s proprietary EASE technology comfort inside. With a rubber outsole, they are particularly suited to hit Soho’s streets cobblestones or any New York rough surface. A 2 ½ heel height gives you a comfortable height without losing balance. Pair them with skinny jeans and wrap yourself in a plaid blanket to walk around town looking stylish and awesome.
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If you are looking for supreme comfort, this Rosa Boot by Vionic footwear offers it in a contemporary style with a 1 ½ inch heel that will grace anything you wear. The shoe features leather, shearling lining and a protective coating against snow or sleet weather. It has a flexible removable microfiber-covered EVA orthotic insert that offers natural alignment support from your feet to your spine. If you walk a lot on New York’s streets, you will appreciate this line developed by the respected podiatrist Phillip Vasyli and founder of orthoheel technology that supports your arch and helps prevent heel pain. Recommended by Dr. Andrew Weil, this line is pure joy for anyone who suffers from foot pain. Match them up with all the styles of the season and find more options. Available in brown and black at

Functional, light and durable yet easy and chic, this Rockport’s Christine full grain leather bootie with a 1.25” leawood wrapped heel is perfect for all your activities whether in town or in the country. Made to be super comfortable with a cozy footbed and a microfiber cover, it has a wide stretch gore on the top to fit snuggly as well. This is the essential easy waterproof booty that you will reach out to over and over to accompany your formal or casual attire for the season. With a pair of leggings, a pencil knife skirt or a sleek pair of cropped flares, it will always be flattering. Available in brown, black or grey at

Inspired by clogs, the light colored sole of these Dansko Maria taupe booties contrast with the black milled nubuck uppers to create a vibrant look inspired by the outdoors and adds a rustic elegance to the classic ankle boot. With a 2 inch heel, the bootie has a cushioned leather wrapped footbed and offers arch support. A roomy, soft rounded toe box ensures your toes never get crushed. This is a fun, easy boot to wear for long stretches of time painlessly and joyfully from fall to spring. Available at

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