I’m no stranger to experimenting with fashion; honestly, I’m typically game to road-test anything, even the season’s most polarizing looks. Something you won’t catch me in, though? Uncomfortable silhouettes—think super-skinny heels, tight jeans, etc. I’m a firm believer that looking chic and feeling cozy aren’t mutually exclusive, especially during these chilly months. And, as luck would have it, many of winter’s top trends hinge on comfort.
As the holidays (and teeth-chattering weather) inch closer and closer, now’s the time to get familiar with feel-good outfits that are cute and, more importantly, don’t look sloppy in the slightest. One such style that has piqued my interest as of late is the humble sweaterdress, aka, the perfect one-and-done look for festive parties. Just add tights and booties, and you’re good to go. Meanwhile, if you’re someone who strays away from denim, might I suggest a soft ribbed pair of pants? They provide the same comfort as your pajamas yet are apt for the outdoors. This is just scratching the surface—keep scrolling to find eight cozy-chic outfits worth emulating from now until spring.
Textured Pullover + Ribbed Pants
Styling notes: There’s no better feeling than snuggling up in a cushy sweater and soft ribbed pants. Simply elevate the casual mash-up with a long luxe coat and pointy flats. High-shine gold jewelry is the perfect finishing touch.
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Suzie Kondi
The Baba Beanie in Luxtweed Cashmere
ZARA
Extra Long Wool Blend Coat
Sporty & Rich
Src Ribbed Trousers
Sweaterdress + Printed Tights
Styling notes: For a polished ensemble that doesn’t skimp on comfort, look no further than a sweaterdress. When wearing your sweats all day isn’t an option, the number is the next best thing. Tip: Ward off goosebumps with thick tights (bonus points for a fun print).
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English Factory
Crew Sweater Dress
Wolford
Multicolored Dot Tights
Staud
Sebastian Kitten Heel Mules
Fair Isle Sweater + Wide-Leg Pants
Styling notes: ‘Tis the season to sport a Fair Isle sweater. And if you’re feeling extra festive? Toss on a bright-red style. As for styling, make the knit the pièce de résistance of your look by slipping into understated black wide-leg trousers.
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Levi’s
Lou Fairisle Crew Sweater
Madewell
Ribbed Turtleneck Long-Sleeve Tee
COS
Relaxed Fluid Wide-Leg Pants
Slouchy Blazer + Balloon Pants
Styling notes: Balloon pants have been a red-hot item this year, and rightfully so. With a voluminous silhouette, it doesn’t get much comfier than these bottoms. If you reside somewhere warm year-round (like me), consider teaming the of-the-moment trousers with a tailored blazer for a sharp getup.
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Abercrombie
The Oversized Blazer in Wool | Taupe Herringbone – 00
Helsa
The Puff Pants in Ultra Premium Jersey
ZARA
Soft Leather Ballet Flats With Bow
Fuzzy Jacket + Matching Hat
Styling notes: Two furry pieces are better than one, so don’t be afraid to double down on the quintessential winter look this season. I’d suggest grounding an ultra-fluffy jacket and coordinating hat with straight-leg jeans and ballet flats.
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Long Jacket + Slouchy Pants
Styling notes: A long coat, like this floor-sweeping silhouette, exudes main character energy. Keep the outfit’s cozy vibes going by way of a wool or cashmere sweater and slouchy trousers.
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Reiss
Maeve Belted Double Breasted Wool Blend Coat
Reformation
Monique Cashmere Mockneck
Teddy Coat + Turtleneck Sweater
Styling notes: Sometimes, your outerwear is the look. Such is the case with this statement-making cream teddy coat. As for styling the jacket, try sticking to a soft pastel color palette throughout your outfit for a cohesive finish.
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J.Crew
Zip-Up Jacket in Textured Faux Fur
J.Crew
Wide-Rib Cashmere Turtleneck Sweater
DL1961
Hepburn Wide Leg High Rise Jeans
Two Sweaters + Silk Skirt
Styling notes: I’ll never bid adieu to my slip skirts, as the piece is just as elevated as it is practical. Kick the comfort up a few notches with a layered sweater look—you won’t regret it.
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Uniqlo
100% Cashmere Crew Neck Jumper
Reformation
Carolina Silk Skirt
J.Crew
Stevie Knee-High Boots in Leather









