5 Outdated Winter Boot Trends We're Ditching and What We're Buying Instead


(Image credit: The Style Stalker/Szymon Brzóska)

As style people (hey there), we've experimented with a slew of winter shoe trends over the years to find those ideal silhouettes that are equal parts fashion and function. Sure, we have many of these perfectly acceptable styles at the ready in our closets, but the change in seasons comes hand in hand with our desire for a wardrobe refresh—starting with a winter-boot upgrade.

So with that in mind, we thought we'd share the winter boot trends we're considering storing away due to their somewhat outdated nature. Alternatively, we're also sharing the styles we're excited to test out this season instead for inspiration if that's of interest. Of course, it's always smart to remember that you should always wear whatever you love, despite someone else's personal preference.

Keep scrolling to uncover the boots we're considering to inspire your next winter shopping haul.

Ditching: Knee-High Lug-Sole Boots

Buying: Sleek Riding Boots


"My shoe rack can only hold so many pairs, and with that, I'll be nixing my knee-high lug-sole pairs. There's no doubt that they're practical for the winter, but I always found them too tricky to style, so I'll be prioritizing sleek riding boots instead that I know I'll have in my closet for years to come."

Ditching: Ankle Boots With Rounded Toes

Buying: Square-Toe Boots


"Simple block-heel ankle boots with a rounded toe are certainly classic, but this winter, I'm still more interested in shopping for boots with square toes. They obviously don't feel as fresh as they once did, which is why I'm prioritizing styles with elongated square toes. They feel especially sophisticated and versatile."

Ditching: Sock Boots

Buying: Structured Knee-High Boots


"I got some good wear out of my skintight sock boots last year, but I'll be putting them aside this winter in favor of more structured leather knee-high boots to wear with my midi skirts, skinny jeans, and long shorts this winter."

Ditching: Standard Ankle Boots

Buying: Pointed-Toe Booties


"I am loving pointed-toe boots this winter. They look so edgy and cool and can totally take an outfit up a notch. I love pairing them with a sweater during the day and then with a pair of tights and a minidress for an evening look. I'm ditching my standard ankle boots this season. I know—I'm shocked too. They feel a little dated to me, and knee-high or thigh-high boots feel so much more elevated."

Ditching: Sock Booties

Buying: Kitten-Heel Boots


"Sock boots had their moment in the sun, but I agree with Judith that their time is over. Right now, I'm into kitten-heel boots."

This article was originally published at an earlier date and has been updated. Next, check out the best basic black-ankle-boot outfits to test out this winter.

Bobby Schuessler
Market Director

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent over seven years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retialers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises. He has also worked across a variety of other media brands and fashion retailers like Refinery29, PureWow, Men's Health, and Gilt covering commerce, trend reporting, women's and men's fashion, home, and lifestyle.