The Experts Agree: *These* Are The 5 Ankles Boots Worth Shopping This Winter (2024)

Timeless and versatile, the best ankle boots of 2023 are absolute wardrobe essentials. Chelsea boots, platforms, kitten heels — whatever your preference, these tried-and-true staples are endlessly versatile. So finding a pair you can dress down with classic denim or up with playful dresses is not difficult... however, picking from the season’s many options can be.

Of course, opting for an of-the-moment silhouette can be tempting. But Alison Bruhn, a wardrobe consultant and co-founder of The Style That Binds Us, warns against fly-by-night catwalk moments. “A few labels are showing Croc-style booties,” Bruhn says. “They are cartoonish in size and style; they look like boots the Seven Dwarves would have worn in Snow White. A few fashion-forward people and influencers will gravitate toward these, but they probably won’t go mainstream in a major way.”

In Bruhn’s opinion, the more enticing ankle boots out there right now are styles that ride the line between on-trend and timeless. “The kitten-heeled suede bootie seems to be everywhere, as does the combat boot,” says Bruhn, noting many of fall and winter’s stand-out silhouettes are quite easy to walk in. “After that, I would say the Western ankle boot. They make sense in a practical way because they are both chic and comfortable, something that people got used to in recent years.” Other persistent trends Bruhn is noticing include shearling-lined ‘Après-ski’ styles (they’re the perfect winter boot) and pointed-toe stilettos.

Shopbop fashion director Caroline Maguire agrees that Western styles and cozy shearling are having a moment. Other things she’s noticing? “I've seen lug sole boots everywhere this past season, and I anticipate folks to continue to incorporate this style into their winter wardrobe,” she says. “Additionally, there is a platform craze! This fun style is expected to stay on trend through winter as well.”

But most importantly, the key ankle boots of the moment are incredibly easy to work into one’s cold-weather wardrobe. “They’ll help you feel stylish on even the coldest of days,” Maguire insists. Keep scrolling to shop TZR’s favorite picks this winter.

The Wild, Wild West

Cowboy boots have long been the cool-girl shoe, and this season is no different. Functional and fun, Bruhn believes a Western-style bootie is the ultimate shoe style for fall and winter. “They are a smart and comfortable option and a little ‘badass,’” Bruhn says. “They are a step up from a sneaker, and you have that rock ‘n’ roll vibe when wearing them.” Saint Laurent has the “ultimate” black leather pair, but Golden Goose’s cowboy ankle boots are Bruhn’s favorite.

Here, Kitty Kitty

Elegant and easy to walk in, a kitten heel bootie will never go out of style. “The kitten heel bootie will stay around because it is very attractive and can be dressed up or down,” Bruhn says. “It fits well in a working wardrobe, and almost anyone can wear the heel height.” Khaite’s suede “Dallas” boots are a great option for those wanting to combine ease and elegance, while J. Crew’s “Stevie” boots come in myriad neutrals and fabrics. Opting for suede? “Always spray suede boots with a protective spray like Cadillac Premium Water Repellant & Stain Protector,” Bruhn advises.

Stomp The Yard

The combat boot craze right now proves you needn’t forego form for functionality. “Combat boots never seem to go out of style in today’s world,” Bruhn says. “They are sturdy, highly functional, and very on-trend. You will see people wearing them with everything from distressed jeans to dresses.” Pairing edgy combat boots with a maxi skirt is one of Bruhn’s favorite looks because it “mixes masculine and feminine aesthetics.” Consider Dr. Martens, like the Jadon Boot Smooth Leather Platforms, your entry point: They are simple, heavy-duty, and will never go out of style.

Maguire agrees. “Every winter, I always return to classic lace-up boots,” she says. Fendi’s special edition “Domino” biker boots combine the best of both worlds. The rubber lug sole on these eye-catching green combat boots provides an added layer of durability and trendiness.

To The Point

“The stiletto heel ankle boot is edgy and sexy,” says Bruhn — although she points out one drawback. “They’re not super easy to wear all day or when commuting.” Luckily, there are plenty of ways to work around this. Choosing a pointed-toe boot with a shorter heel is a great way to capitalize on the style’s sexiness without sacrificing sensibility. Balenciaga’s blinged-out “Cagole” booties are a great example of this. With an understated 70mm heel, these shoulder bag-inspired shoes are striking, yet practical enough for everyday wear.

Soft Messaging

If this season’s winter jacket trends have taught us anything, it’s that coziness will continue to reign supreme. And what’s cozier than a pair of shearling-lined ankle boots? “Hiking boots with shearling are such a fun trend,” Bruhn tells TZR. “They’re a great mix of feminine and masculine — think Aprés Ski with leggings and an oversized sweater by the fire.” Prada’s black leather “Brixxen” boots are a sleek, monochromatic option, while Inuikii’s sneaker-inspired shoes with braided laces and ultra-fluffy shearling are casual and classic.