13 Best Ankle Boots for Women, According to Style Pros

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$295

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$90

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By Rachel Mosely

When it comes to comfort and style cred, it's hard to outmatch the ankle boot. Equally suitable for a day at the office, a night out or an errand run, the bootie is a cornerstone of a functional winter wardrobe. The real challenge is finding the perfect pairs for your lifestyle, climate and wardrobe. To that end, we’ve asked fashion stylists to share their favorites—the ankle boots they snap up for their clients and themselves. Read on for their go-to pairs.

$592 at Zappos

$650 Save $58

Mini pearls add the perfect amount of flair to these Chelsea-style boots, a favorite of New York City-based stylist and brand consultant Ashley Afriyie. "The pearls add a dressy element to it, so you can just as easily wear them for a special occasion as you can running weekend errands," she says. Because of its versatility, the combat style works well with jeans, a T-shirt and a leather jacket, or a turtleneck, mini skirt plus your favorite fall coat, Afriyie notes. Plus, with a thick sole and durable leather, the pair is built to last.

$89 at Zappos

$139 Save $50

Nashville, Tenn.-based stylist Molly Russell knows a thing or two about boots, and she's partial to this pair, which is simple enough to work as an everyday shoe—but also unforgettable, thanks to the great detailing. The trail of gold studs "adds visual interest, while still keeping the pair classic and versatile," Russell says. At almost 4 inches, the heels on this boot (available in Black, Cream and Teal) supply altitude and pair well with a crop pant or midi hemline.

$820 at Bottega Veneta

Everyone needs a reliable pair of mud-and-slush-proof slip-ons, and Los Angeles-based stylist Miso Dam, who gives these rubber ankle boots high marks for style and comfort. "I have these by my front door to slip on whether I’m taking my dog to the park or spending an entire day on set," she says of the cotton-lined molded boot. "I’m all about ease—I love that there's no zipper or buckle on them, and they look even better when they’re a little beat up."

$198 at Schutz

A sculptural, translucent heel and sleek pointed toe give this pair—a go-to of Atlanta-based wardrobe and prop stylist Melissa Young—instant wow factor (not to mention body-elongating powers). "I love a white boot, and recommend these to my clients who wish they were a tad taller," Young says, referencing the slender, see-through, 4-inch heel that adds plenty of height without clunkiness. To amplify that effect, she suggests going monochrome with ivory pants: "Pairing the same color shoes as your pants gives instant long legs," she explains.

$385 at Sandro

$385 at Farfetch

With a buttery suede exterior and a comfortable 2-inch heel, this boot adds understated sophistication to any look. New York City-based stylist Andrew Franco appreciates their ability to elevate a casual everyday outfit; he recommends combining them with a slim pair of jeans and an oversized jacket for low-key elegance.

$296 at Saks Fifth Avenue

$395 Save $99

$395 at Staud

This modern spin on a kitten heel boot comes in five different hues of nappa leather and suede to suit any style personality. Says Los Angeles-based stylist Marisa Ledford of this bootie with a pointed rectangular toe, "I’d style them with a pair of straight-leg jeans and an oversized half-zip sweater for a chic minimal look."

$295 at Zappos

The right low boot can transition from day to night, and that's the appeal of this sleek Coach pick, Afriyie says. "What I love is even though they’re technically a high-heeled pair, they’re comfortable enough to wear all day," she says. The gold buckle gives the boot a bit of visual oomph without competing with your overall look, she notes, adding she has styled them with everything from skinny black jeans and a sweater for a casual event to a dress, trench coat and tights for a night out.

$45 at Zappos

$90 Save $45

$45 at Nordstrom Rack

$90 Save $45

You don't have to sacrifice form to have a functional day boot. Russell recommends this block-heeled pair: the sturdy heel makes it comfortable to wear all day and the subtle strap detailing keeps it from feeling too utilitarian. She suggests playing up its simple elegance with a top and pant in the same hue (it's also available in Black and a rich, warm Tan), then topping off the look with a patterned wool coat.

$1,390 at Gucci

When it comes to splurge territory, Young favors this Gucci ankle boot, which offers a feminine twist on a menswear-inspired look—one of her favorite trends. She describes it as "loafer and ankle boot at the same time," and styles it either with a mini dress and tights, or a trench coat with black turtleneck and jeans. Crafted in Italy with luxurious details like a gold-plated heel, it's a timeless investment piece that’ll add a pop to outfits well beyond this winter.

$300 at Ssense

$390 Save $90

Just as essential a wardrobe staple as the little black dress, the little black boot is a simple, wear-it-with-anything piece that "will always be chic," Franco says. His favorite version? This pair from Staud, made of goatskin leather for a soft, almost velvety finish. The stacked heel gives it a comfortable base (plus at under two inches high, it's not an intimidating heel), and the elasticized sides make the shoe easy to slip on with your favorite pair of jeans.

$1,200 at Moda Operandi

$1,200 at Nordstrom

In search of some statement footwear? Ledford loves the cowboy-inspired stitching, slim curved heel and dramatic elongated square toe of this Italian lambskin pair, which she calls "a city girl's take on a Western-style boot." She suggests adding them to a midi dress and slouchy bag "for an effortlessly cool vibe."

$996 at Ssense

$1465 Save $469

$1,725 at Nordstrom

"There's nothing I love more than a chunky heeled black boot," says Dam, who has integrated this pair into clients’ wardrobes—and her own. The luxe, sky-high calfskin platforms prove ankle boots don't have to be low-profile. Dam says this boot works beautifully with a babydoll dress or casual denim looks, thanks to a 6-inch heel that's "so major—and essential for short gals like me."

$100 at Mango

This Chelsea boot also earns a spot on Russell's list of must-have winter booties. Its chunky lug track sole makes it a particularly practical pick—you can wear it while navigating rain-slicked streets or trudging through slush without getting your feet wet. All in all, it brings street style to the everyday wardrobe.