The 31 Best Winter Shoes You Need the Most This Season

last updated 5 February 2021

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If you hate people complimenting your clothing and your style, then keep scrolling, because this shopping roundup of winter shoes does not mess around. This shoe shopping haul features all the shoes you would want in a dream winter wardrobe and then some. Keeping a variety of climates in mind, ahead you will see everything from dreamy holiday heels to chunky weather-proof boots and each style is more eye-catching than the next.

In order to stay on the compliments theme, I will admit that some of the shoes ahead might not look like the most practical option, but that wasn't really the goal. While there are certainly some versatile and reasonable soles in here (flat boots, house shoes, etc.), I wanted to also throw in some shoes that simply put a smile on your face and will make others feel so strongly about your footwear selection, the can't help but come up to you to say something.

Song of Style

Brit Boot in Camel

From the color to the heel, these are sheer perfection.

Mango

Leather High-Leg Boots

The fresh way to wear chunky boots—chocolate brown.

Zara

Faux Fur Lined Buckle Clogs

What's better than clogs in the winter? Faux fur lined clogs.

Porte & Paire

Chain-Embellished Leather Point-Toe Flats

These flats are seriously chic.

Staud

Wally Boots

Embrace the patchwork trend with these stunning boots.

H&M

Chunky Leather Loafers

The perfect chunky loafer.

Tibi

Collier Boots

Wide-calf boots are always a good idea.

Converse

Chuck Taylor All Star Canvas High-Top Platform Sneakers

Even if you already own tons of Converse, this lug-sole version is a must.

Sam Edelman

Samira Boots

These look way more expensive than they actually are.

Zara

Leather Square Toe Heels

Clearly, we love a chain-adorned shoe around here.

Wandler

Isa Boots

These Wandler boots are on every fashion girl's wish list.

Birkenstock

Arizona Shearling Sandals

Practical and cute.

Tory Burch

Square Toe 20mm Boots

These flat boots will look great with all of your dresses and skirts this season.

By Far

Stevie 42 Boots

Good luck resisting this buttery hue.

Manolo Blahnik

Hangisimu Embellished Satin Mules

Everyone needs a glamorous shoe around the holidays, even if you're just staying at home.

Vince

Kellen Boots

This boot is a perfect 10.

Jeffrey Campbell

Tanked Chelsea Boot

Boots that aren't black? Yes, I think you'll survive.

Mango

Heel Leather Shoes

There's something about chocolate brown that feels irresistible this season.

Schutz

Dynora Fuzzy Slides in Camel

House shoes just make sense right now.

Neil J. Rodgers

Eva

These boots will be in style forever.

Proenza Schouler

Tied Kitten Mules

Okay, these are seriously cute.

Proenza Schouler

Glossed-Leather Pumps

Preppy school girl shoes are trending and this pair is IT.

Vagabond Shoemakers

Cosmo 2.0 Chelsea Boot

If you don't own simple chunky black boots yet, the time is now.

H&M

Thigh-High Boots

Miracles do happen.

Khaite

Palermo Gathered Satin Pumps

These are just as chic in black.

Nike

Air Vapormax Plus Sneaker

These black sneakers will make your winter ten times cooler in seconds flat.

Zara

Tall Leather Boots

Just do it.

Mango

Faux Fur Felt Sandals

The coolest house shoes we ever did see.

JW Anderson

Chelsea Boots

If you're drooling over these, you aren't alone.

Tamara Mellon

Easy Rider Mid Calf 35

I own these and can't sing their praises enough.

Topshop

Hondouras Brown Western Leather Boots

A classic shoe that fashion girls cannot stop buying.
Next up, shop the most important handbag trends of 2021.

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Lauren Eggertsen is currently the editorial director of Who What Wear and has worked at the company for over eight years, where she started as an associate editor and has since worked her way up. Lauren has over 10 years of experience in the fashion editorial space, starting her career with internships at Marc Jacobs, Marie Claire, and The Zoe Report, where she was later hired as their editorial assistant. Lauren has worked in the Los Angeles and New York Who What Wear offices but currently calls L.A. home. It is here where she leads and manages Who What Wear's fashion team and oversees all day-to-day editorial content and large tentpole moments. This includes all of the runway, trend, and shopping-driven content that ultimately helps to build a strong brand reputation within the industry. Lauren's role also includes helping to set the fashion direction for all original photo shoots and often styles many of the celebrity cover shoots, including big names like Kaia Gerber, Normani, and Kristen Stewart.

She has also attended multiple fashion weeks, including New York, London, Milan, and Paris, where her personal style has been featured on sites such as Vogue, Harpers Bazaar, and Elle. She prides herself on discovering and supporting small brands and on her knack for a good vintage shopping find. When she isn't working, she enjoys researching and dining at reputable restaurants around both her neighborhood and the globe.