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44 Best Booties to Compliment Your Cold-Weather Outfits

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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.

If 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. Sock 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 44 of the best.

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. For a nod to the sock-boot trend, opt for The Row’s Liisa pointed-toe bootie; for a slightly looser fit, consider Khaite’s Ona boot.

The Row

Liisa pointed toe booties

Chelsea Booties

When it comes to booties, the Chelsea boot remains the ultimate classic. Effortless in shape and timeless in appeal, it’s the fail-safe option every wardrobe needs. Versatile enough to style with anything, it’s destined to become your day-to-day shoe this fall. Opt for Tom Ford’s sleek, narrow take or go for a height boost with Saint Laurent’s lug-sole version.

Zara

buckle detail ankle boots

Brunello Cucinelli

bead-embellished ankle boots

Lace-Up Booties

To make a bold statement this fall, look no further than the lace-up bootie. Offering just the right mix of grunge and ease–there are versions suited for every occasion. Go practical with Gucci’s everyday walker, office-ready with Tove’s sleek low-cut style, or after-dark glam in Jimmy Choo’s stiletto take.

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 weatherproof Chelsea style or a pull-on design with a zip (The Row’s version has become a perennial go-to), we love these with rigid denim and relaxed tailoring or contrasting feminine attire.

Block-Heel Booties

Whether you prefer a leather or suede bootie, with a pointy or a square-toe, a block-heel style in a neutral color, will go the distance in your wardrobe, pairing effortlessly with outfits centering around jeans, trousers, or dresses. It’s a walkable shoe choice (especially in a low heel) that you’re sure to lean on when styling out your looks.

Zara

split leather ankle boots

Maison Margiela

Tabi split-toe leather ankle boots

Flat Booties

Flat suede and leather booties, i.e. 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 with round toes feel especially fresh this season—from Khaite’s slim animal-print Colt boot, already an editor must-have, to Isabel Marant’s Stania, a winter-boho take with a studded strap. Flat, but far from basic, these silhouetted offer a modern refresh on an everyday classic.

Minimalist Booties

Ultra low-cut ankles bring minimalist booties into the future. Showing more of the leg than your typical ankle boot, the silhouette feel extremely contemporary. Whether you preference leans toward a kitten heel or proper pump, a square-toe or razor-sharp point, the options are endless—with designs from go-to labels including Phoebe Philo, The Row, and Alexander McQueen.

High-Heel Booties

To complement dressier 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 hues and materials, from classic black leather boot to of-the-moment burgundy. Don’t overlook unique elements like subtle embellishments (see: Gucci’s horsebit) or a two-toned, toe-cap.

Animal-Print Booties

On the fall 2025 runways, animal print added just the right touch of edge to accessories, and booties were no exception. An easy way to elevate a casual look, step into Khaite’s snakeskin flat boot for day-to-day strolling, or add a bit of height with Christian Louboutin’s leopard-print ankle bootie for a night out on the town.

Cozy Booties

If comfort is what you orient your fall boot collection around, a touch of shearling is the ideal way to embrace it. Whether you’re leaning weatherproof with one of Ugg’s bestsellers, fashion-forward, or belted like with Balenciaga’s, these styles play perfectly with a pair of jeans or leggings for a cozy Sunday stroll.

Weather-Ready Booties

A weather-ready bootie, from cropped snow boots to wellies made to take on the elements, will surley be your most worn in inclement weather and winter. When comfort takes precedence, shearling-lined and pillow-y quilted styles are the coziest choices. Add a pop of red with Hunter’s iconic Wellie bootie, or brave subzero temperatures in style with Moon Boot’s Luna shearling pair. Functional yet fashion-forward, these cold-weather staples prove practicality can still make a statement.

Moon Boot

Luna shearling snow boots

#Booties #Compliment #ColdWeather #Outfits

Tags: BootiesBootsColdWeatherComplimentfall fashionOutfitsshoeswinter fashion
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