54 Best Booties to Compliment Your Cold-Weather Outfits

The best booties for women are unquestionably one of the most versatile fall footwear styles for everyday outfits and occasions alike, coming in leather, suede, haircalf, and more. Yes, the boot market is rife with options for all shoe preferences, from kitten heels to knee-high silhouettes. However, ankle-grazing silhouettes are supremely versatile, whether you’re tucking them under classic denim, like the best straight-leg jeans, or showcasing them with midi hemlines in the form of the best fall dresses, like cozy-chic sweater dresses and denim midiskirts.

The Best Booties, According to Vogue:The Low-Cut: Toteme The Wide Shaft ankle boots, $820The Kitten Heel: Madewell The Dimes kitten-heel boots, $198The Classic Lug: Banana Republic tall Chelsea boots, $280The Block-Heel: Aeyde Linn leather ankle boots, $495The Fashionable Flat: Khaite Marfa ankle boots, $1,350The Striking Heel: Emme Parsons leather stiletto ankle booties, $795The Stretchy Style: Reformation Onya ankle boots, $378The Sculptured Stunner: Bottega Veneta Lewis square-toe ankle boots, $1,700The Weather-Ready Pair: Ganni outdoor Chelsea boots, $475If you’re wondering about the difference between a bootie and a boot, let us explain. A bootie is identifiable by its shorter stature, usually hitting around the ankle, just above or below. On the other hand, boots are designed to sit higher on the leg, ranging from mid-calf to over the knee. Some booties are cut loose, while others hug like a sock and can be heeled or flat. So, no matter if you’re the stiletto type or live for easy-to-walk-in designs, there’s undoubtedly a bootie for you this season.

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 BootiesThis 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.

Toteme

The Wide Shaft ankle boots

Reformation

Gretel ankle boots

Tod’s

square-toe zip ankle booties

3.1 Phillip Lim

ID Glove ankle booties

Kitten Heel BootiesTry 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.

Madewell

The Dimes kitten-heel boots

Aeyde

Zoe snake-effect ankle boots

M.Gemi

The Delfina booties

Toteme

slim patent zip ankle boots

ATP Atelier

Polverelli bootie

Lug-Sole BootiesIf 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.

Prada

Monolith Chelsea boots

Vince

Cabria Lug lace-up boots

Loeffler Randall

Reggie leather Chelsea ankle booties

Banana Republic

tall Chelsea boots

Veronica Beard

Delilah leather booties

Block-Heel BootiesWhether 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.

Aeyde

Linn leather ankle boots

Margaux

The Downtown boots

Stuart Weitzman

Yuliana stretch leather ankle booties

Flat BootiesFlat 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.

Yuni Buffa

Nightingale suede boots

Le Monde Béryl

Luna leather ankle boots

Robyn mixed leather short boots

Massimo Dutti

Greased split suede ankle boots

High-Heel BootiesWith 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.

Khaite

Nevada stretch high boot

Emme Parsons

leather stiletto ankle booties

Proenza Schouler

60 leather ankle boots

Saint Laurent

Faubourg buckle ankle boots

Stretch BootiesThe 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.

Reformation

Onya ankle boots

Gucci

Horsebit ankle booties

Toteme

The Sock leather ankle boots

Khaite

Apollo flat ankle boots

Proenza Schouler

55mm stretch ankle boots

Sculptural-Heel BootiesYour 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.

Bottega Veneta

Lewis square-toe ankle boots

Dries Van Noten

suede ankle boots

Alexander McQueen

leather sock boot

Aquazzura

95mm Amore ankle boots

Souliers Martinez

Teo snake-effect ankle boots

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.

Ganni

outdoor Chelsea boots

Miu Miu

shearling Chukka booties

Bottega Veneta

Haddock leather ankle boots

Manolo Blahnik

Tomosa suede boot

La Canadienne

Abba suede shearling waterproof booties