8 Outdated Winter Boot Trends We're Ditching—and What We're Buying Instead

The Best Winter Boots You Can Buy


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So with that in mind, we thought we’d share the winter boot trends we’re considering storing away due to their somewhat outdated nature.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. From gorgeous knee-highs to lace-up stompers, keep scrolling to uncover the boots we’re considering in and out to inspire your next winter shopping haul.

Ditching: Duck boots
Buying: Thick-sole styles

“A few years back, I was into the idea of super-clunky, rubber-all-over, lace-up duck boots for winter. Now those feel like too much for me, and instead, I have my eyes on more streamlined pairs with thick rubber soles but sleek uppers.”

Ditching: Hiking boots
Buying: Combat boots

“Hiking boots had a moment there last winter, and while I can’t deny how practical they are, I can’t say I’ll be lacing up my own pair with a fashiony outfit anytime soon (wearing them for actual outdoor adventures is a different story, though). Instead, I’m fixated on combat boots and plan to wear my Dr. Martens a ton in the coming months. They’re chic and equally as practical—what’s not to love?”

Ditching: Stiletto booties
Buying: Slouchy knee-highs

“Right now, I’m abandoning boots with super-high stilettos. Instead, I’m wearing styles with lower heels like this slouchy knee-high version.”

Ditching: Basic lace-ups
Buying: Statement lug-soles

“While I’m all for basic black ankle boots, I’m considering storing the somewhat boring smooth lace-up boots I’ve worn the last few winters. It’s all about eye-catching, lug-sole boots in unexpected colors with unique details like shearling to make a practical statement this season.”

Ditching: Sock boots
Buying: Structured knee-highs

“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: Rounded-toe ankle boots
Buying: Square-toe boots

“Simple block-heel ankle boots with a rounded toe are certainly versatile, but this winter I’m shopping for boots with interesting details like square toes, sculptural heels, or interesting textures (e.g., snakeskin and croc embossing).”

Ditching: Chelsea boots
Buying: Platform boots

“This season, I’m ditching classic chelsea boots for something a bit more daring—platforms. I’m planning on wearing them with everything from dresses to tailored trousers.”

The best winter boots of 2020

Ditching: Sock boots
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, and the J.Crew versions below surprised me in the best way.”

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