5 winter boots trends to get ahead of now

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Lauren Caruso is an In The Know shopping contributor. Follow her on Instagram and Twitter for more.

Depending on where you live, winter could be a season filled with blistering snowstorms and caustic 60 mile-per-hour winds — or it could be a temperate, mild few months where the weather hovers around 50 degrees. No matter what sort of season you’re prepping for, there’s a good chance you’re starting with your boots. 

The good news is that some of 2021’s winter boot trends were made for harsh weather: The lug-sole trend we’ve seen for the last few seasons has ventured even further into hiking boot territory. But this season’s hiking-adjacent footwear isn’t just functional — many styles also feature fashion-forward details like contrast stitching, color-blocking and elastic insets for a comfortable fit. Platform boots are also fairly weather-friendly depending on the style. Brands like Simon Miller, Nodaleto and Valentino were all ahead of the heightening look.

Other trends aren’t as blizzard-ready, like the resurgence of the stiletto heel. After four straight years of chunky, bulky heels trending for everything from sneakers to mules, the thinner, sleeker stiletto has made a comeback on boots of all heights. Still, there’s something refreshing about the return of a more slender silhouette.

Below, see the top five winter 2021 boot trends to get ahead of now, plus my favorite shopping picks to get the look.

Stiletto Heel

This winter brings on a whole slew of trends — and not just because it’s a new season. After 18 straight months of sweatpants, sneakers, and other work-from-home loungewear, we’re all craving a little elegance. And what’s more elegant than the stiletto?

While the chunky heel will never go away, this season, a second-skin, knee-high boot is especially on the rise — and it’s sexier than ever. You can go the traditional pole-thin stiletto route or, if you crave a little more stability, choose a style with an illusion stiletto, which appears paper-thin from the side, but stretches across the entire back of the heel. Wear yours with a mini skirt while you can — and later, layer them with a billowy, flowing midi dress.

Mango High Heel Leather Boot, $249.99

Credit: Mango

Zara Stretch Fabric Ankle Boots, $69.90

Credit: Zara

Schutz Mariana Boot, $238

Credit: Schutz

COS Leather Sock Ankle Boots, $285

Credit: COS

Hiking-Inspired Boots

The lowly hiking boot enjoyed a rebrand in recent years, and this season, it’s even more fashionable than ever. While some iterations stick to the functional silhouette’s lace-up closure and lug sole, others go outside the box of practicality with fun details like color-blocking.

Alohas Can Can Boot, $170

Credit: Revolve

Proenza Schouler Shearling Hiking Boots, $795

Credit: Shopbop

Leather Boots with Tall Leg, $199.99

Credit: Mango

Staud Bow Boot, $450

Credit: Shopbop


The knee-high boot is a perennial favorite for myriad reasons, but chief among them is this: It can make any basic outfit feel, well, instantly less basic. Whether you opt for a skin-tight fit or prefer something looser around the calf, the right knee-high boot can elevate a Canadian tuxedo, polish a traditional suiting look or even make a blah skirt sing.

Looks Like Summer Kira Knee High Boot, $138.95

Credit: Looks Like Summer

Ulla Johnson Jett Printed Calf-Hair Boot, $418 (Orig. $930)

Credit: The Outnet

Reformation Nylah Knee-High Boot, $398

Credit: Reformation

Yuul Yie Doris Long Boots, $800

Credit: Yuul Yie


Made popular by brands like Nodaleto and Simon Miller, the platform boot is the natural evolution of the corresponding ‘90s trend that we’ve seen in recent summers: the platform mule. Some veer more practical, like LAST’s hiking-inspired platform Chelsea boot, while others lean into the nostalgia of decades past with a groovy, Studio 54-inspired double platform heel.

Simon Miller High Raid Boot, $670

Credit: Revolve

LAST Trail Chelsea Boots, $300

Credit: Shopbop

Zara Heeled Leather Crepe Ankle Boots, $199

Credit: Zara

Steve Madden Cobra Black Leather Boot, $159.95

Credit: Steve Madden

Oxford-Crossover Boots

Sure, technically speaking, oxfords aren’t boots. But the chunkier, lug-sole styles hitting the market this season certainly serve the same purpose. Style them with calf-high socks and a pleated skirt for a fun fall look now, and swap out the skirt for trousers or cuffed jeans when winter hits. (Maybe don’t throw these on for a snow day.)

Mango Track Sole Leather Shoes, $129.99

Credit: Mango

3.1 Phillip Lim Kate Oxfords, $550

Credit: SSENSE

Marc Fisher Dorin Lug-Sole Oxford, $99.99 (Orig. $170)

Credit: Marc Fisher Footwear

Prada Monolith Derby, $995

Credit: Nordstrom

If you enjoyed this story, check out the 7 fall trends Lauren Caruso is already wearing!

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