54 Best Booties to Compliment Your Cold-Weather Outfits

Flat or block-heel booties are some of the best for everyday style, pairing flawlessly with trousers, denim, and dresses. Look to other heeled types like a stiletto bootie, perhaps one with an eye-catching sculptural heel or a more modest kitten heel, for more dressed-up moments. Stretch booties are most commonly associated with the ankle-grazing category—they tuck nicely under slim denim and trouser hems while cinching tightly to beautifully elongate legs with dresses and skirts.

Then, there are the more rugged takes on booties, many of which are ideal in the elements. Think trendy lug soles, lace-up combat silhouettes with a practical flare, and weather-ready designs from fleece-lined to water-resistant. To shop Vogue’s edit of stylish booties for every occasion and taste, keep scrolling for 54 of the best.

Low-Cut Booties

This season’s power player in the footwear game happens to be a bootie with a low-cut shaft. These show more of the leg than your typical ankle boot and feel extremely contemporary with designs from some of our favorites such as Toteme, Neous, and A.Emery. Whether you’re a kitten heel aficionado or prefer a proper pump, we’ve covered all the heel heights here, too. These boots prove less is most definitely more.

Kitten Heel Booties

Try a kitten heel bootie for a more delicate look that’s just as easy to walk in. They’re decidedly modern with cropped denim and pair beautifully with more feminine silhouettes like sweeping midi-dresses and skirts. Angled, knife-edge, and pointed toe designs exude maximum freshness, and fall in tow with fall’s trend-forward footwear.

Lug-Sole Booties

If you hadn’t noticed, chunky, ’90s-inspired footwear is everywhere, and the trend most certainly extends to booties. Whether you opt for a lace-up, combat-inspired style with utilitarian flare or a pull-on design with a zip (The Row’s version has become a perennial go-to), we love these best with rigid denim and soft suiting or contrasting feminine attire.

Block-Heel Booties

Whether you prefer leather or suede, a block-heel bootie in a neutral color like black and tan (or this season’s hit: espresso brown), will go the distance in your wardrobe, pairing effortlessly with outfits centering around jeans, trousers, or dresses. It’s a walkable shoe choice that you’re sure to lean on.

Flat Booties

Flat booties, or those designed with a barely-there heel of an inch or less, are some of the most walkable for those seeking comfort and chic practicality. Minimalist styles feel freshest for the season, from sharply pointed silhouettes from Khaite, whose Marfa boot is an editor must-have, to modern square-toe shapes and comfy-classic rounded designs, in suede, stretch leather, and more.

High-Heel Booties

With your most elegant outfits, like a cocktail dress or suit, go for a high-heel bootie in sleek leather. Pared-back aesthetics will favor ultra-streamlined silhouettes in versatile tones, from dark chocolate to bold black. However, don’t overlook unique elements like patent leather textures or a two-toned, toe-cap, or subtle embellishments like a small buckle or decorative pull.

Stretch Booties

The stretch bootie is the silhouette to go for when seeking a slim fit through the ankle. Whether you’re in the mood for a low kitten heel, timeless block heel or this season’s flat, space-age feeling options, your favorite pair will effortlessly tuck under narrow pant legs or complement a range of dress styles. For an ultra-glove-like fit, go for a knitted design.

Sculptural-Heel Booties

Your most fashion-forward bootie is unquestionably a sculptural-heeled style. Whether smoothly curved, angular and geometric, or chunky and metallic, this eye-catching component, while often subtle, instantly up-levels any fall outfit while showcasing your discerning eye for detail.

Weather-Ready Booties

From cropped snow boots and wellies to hikers made to take on the elements, a weather-ready bootie will surely be your most worn in inclement weather and winter. When comfort takes precedence, shearling-lined and pillow-y quilted styles are the coziest choices.