5 Cozy Winter Outfits That Celebrate Your Personal Style

If fashion historians were to look back on 2020, we suspect they’d either shake their heads in incredulity or smirk in bemusement at how much we, collectively, fell into a pit of singular dressing: nap dresses (more so designed to be photographed in rather than actually sleep in), tie-dye anything, and sweatsuits saturated in every color imaginable. In our defense, outfitting ourselves in comfort clothing — and participating in a shared fashion experience — is, really, the only way to wield control when life feels completely and utterly chaotic. 

That’s not to say this year marks the end of individualistic style. With the end of 2020 fast approaching (subtext: a new year, a clean slate, a glimmer of hope), this is the time to reclaim our stylistic preferences from pre-pandemic times. If not now, then when? To help re-familiarize yourself with non-sweats, we partnered with Cuddl Duds to put together five outfits that both harness the power of layering to keep you warm this winter (without feeling weighed down) and celebrate your personal style. 

The Cozy Minimalist 

You love: finding comfort in monochromatism, a neutral color palette, and clean lines. Bright colors and patterns intimidate you (or outright frighten you), but, rest assured, your look is anything but boring. 

Your outfit: a white turtleneck as your base with warm camel-colored layers on top, made even cozier with delectable textures, like a chunky cashmere sweater and a ribbed knit skirt. 

Cuddl Duds Softwear With Stretch Long Sleeve Turtleneck, $, available at Cuddl Duds

Naadam Marled Cashmere Turtleneck Sweater, $, available at Naadam

Zara Knit Midi Skirt, $, available at Zara

H&M Wool-blend Coat, $, available at H&M

Brother Vellies Ronstadt Boot in Cognac, $, available at Brother Vellies

The No-Frills Pragmatist 

You love: anything that doesn’t get in the way of your busy lifestyle. You don’t have time (nor the patience) to give your outfit more than two minutes of thought. And as someone who runs cold, you especially love layers that promise extra insulation.

Your outfit: no-nonsense layers, complete with a double-breasted coat for a look that’s equal parts polished and casual, making it the perfect ensemble for a day of errands. 

Cuddl Duds Softwear With Stretch Long Sleeve Crew, $, available at Cuddl Duds

Mango Wool double-breasted coat, $, available at Mango

Cuddl Duds Double Plush Velour Legging, $, available at Cuddl Duds

Cuddl Duds Womens Chunky Braid Texture Knee High Sock, $, available at Cuddl Duds

Vans Old Skool Sneakers, $, available at Vans

Cuddl Duds Fleecewear With Stretch Full Zip Vest, $, available at Cuddl Duds

The Loud-And-Proud Maximalist 

You love: colors (the brighter, the better), patterns, and unexpected combos. You thrive off of bold and exciting outfits. To put it plainly, you’re an exhibitionist. 

Your outfit: print meets fluorescent hues with a cheetah-print base layer and neon pink pants. Anyone can wear a coat in the winter, but what about a shin-length puffer vest in pearlescent white? That’s all you.


Cuddl Duds Softwear With Stretch Long Sleeve Crew, $, available at Cuddl Duds

TNA The Super Puff™ Long Vest, $, available at Aritzia

Christopher John Rogers Neon wool-blend pants, $, available at Net-A-Porter

Loq Monica Boot in Crema Crinkle Patent, $, available at LoQ

The Great Outdoorswoman 

You love: the wilderness. Even though you may be a city dweller, you get a kick out of applying aspects of your mountaineering look to your everyday life (the idea being: If it can withstand an arduous hike, then it can certainly weather a leisurely walk in the snow). 

Your outfit: a solid foundation of base layers (a wear-everywhere henley and cozy plaid leggings) embellished with key add-ons, like an oversized fleece (pro tip: shop the men’s section) and cool trek-inspired lugsole boots. 

Cuddl Duds Softwear With Stretch Ribbed Long Sleeve Henley, $, available at Cuddl Duds

CBAAF Oatmeal Hoodie, $, available at CBAAF

Patagonia Men's Classic Retro-X® Fleece Jacket, $, available at Patagonia

Cuddl Duds Softwear With Stretch High Waist Legging, $, available at Cuddl Duds

Nomasei Slalom boots in white, $, available at Nomasei

The Romantic Botanist 

You love: diaphanous dresses, dreamy colors, and flowers (it’s your favorite print) — a style ethos that’s pretty much directly at odds with winter. 

Your outfit: a cold-weather version of something you’d wear in the summer (a pretty sheer dress, flower-pressed earrings, and baby yellow slingbacks), with the help of fleece base layers.

Cuddl Duds Fleecewear With Stretch Long Sleeve Crew, $, available at Cuddl Duds

Ganni Organza Dress, $, available at Ganni

Cuddl Duds Fleecewear With Stretch Legging, $, available at Cuddl Duds

Dauphinette Woodland Orchid Earring, $, available at Dauphinette

& Other Stories Relaxed Single Breasted Coat, $, available at & Other Stories

Yuul Yie Zizi Sling-Backs Baby Yellow, $, available at W Concept

Like what you see? How about some more R29 goodness, right here?