If it were up to me, I would spend my winter days hibernating on the couch in snug sweatpants while binge-watching wholesome Christmas movies. But my social calendar is already swiftly filling with places to be. Since lazing around in sweats all season long is impossible, I’ve set my sights on the best (comfortable) winter dresses that will lend themselves to my actual needs: various events, casual gatherings, and upscale cocktail parties.
Fortunately, the market is filled with a ton of cold-weather options that still fit my style. Labels like Banana Republic and Ralph Lauren offer classic closet mainstays like turtleneck sweater dresses with a blanket-like feel and slightly oversized shirt dresses with ample coverage. Other designers are leaning into the latest winter fashion trends—just take a look at Farm Rio’s ruffled leopard print slip-on or En Saison’s olive green gown. And to no surprise, some brands have already begun to roll out holiday-ready dresses stitched with dazzling metallics and silky fabrics (I’ve got my eyes on styles from Bardot and Misha).
Determined to build a steady rotation of winter dresses that will carry me through any occasion throughout the season, I’ve perused hundreds of options across several retailers. If you’re also looking to enhance your collection of winter dresses, follow my lead and shop the edit ahead.
For Casual Outings
Instead of a tailored number for a laid-back event, consider an easygoing alternative that conveys a more relaxed message. Slip into a simple sweater dress crafted with fuzzy wool, or try a dependable denim dress that showcases an edgier appeal. If you decide on a thigh-skimming silhouette, you can cover your legs with tights and a great pair of knee-high boots.
Banana Republic Oversized Fuzzy Alpaca-Blend Sweater Dress
Madewell Denim Tie-Waist Midi Shirtdress
Aritzia Contour Series Dress Second-Skin Longsleeve Turtleneck
Reformation Ozzy Regenerative Wool Sweater Dress
Simon Miller Axon Knit Dress
& Other Stories Long Sleeve Wool & Cotton Blend Rib Sweater Dress
J.Crew Relaxed Cable-Knit Sweater Dress
Rag & Bone Long-Sleeve Knit Maxi Dress
Barbour Beatrix Cable Stitch Long Sleeve Wool Blend Sweater Dress
For Upscale Occasions
Whether you’ve made dinner reservations with your friends at a fancy hotspot or you’re meeting up with that special someone for a romantic date night, you’ll need a winter dress that strikes a balance between sultry and sophisticated. Feel free to experiment with sculpted shapes, off-the-shoulder necklines, and even daring slits, provided that you’re in the mood to make a statement. Needless to say, your wardrobe of going-out outfits will be happy to see these styles coming.
Solid & Striped X Sofia Richie Grainge the Soglio Dress
Farm Rio Leopard V-Neck Midi-Dress
LPA Lainey Maxi Knit Dress
SER.O.YA Melonie Knit Maxi Dress
Norma Kamali Long Sleeve Drop Shoulder Side Slit Gown
Ralph Lauren Tie Front Dress
Michael Costello X Revolve Gregory Gown
Shona Joy La Lune Cumulus Silk Backless Lace Split Maxi Dress
For the Office
For those moments when you want to give your sharp suits a break, soften things up with a straightforward winter dress that looks just as refined. The edit below features crisp collars, formal fabrics, and, most importantly, corporate-friendly hemlines that fall below the knees. Champion minimalism with neutral tones and streamlined designs, or take an ornate approach with playful Peter Pan colors, abstract patterns, and dynamic pleats.
Reiss Winslet Long Sleeve Sweater Dress
Tout a Coup Ruffle-Collar Puff-Sleeve Midi Dress
ASTR the Label Sekani Dress
Banana Republic Wool-Blend Asymmetric Midi Dress
Diane von Furstenberg Geo Print Long Sleeve Midi Wrap Dress
Mango Long Sleeve Satin Midi Shirtdress
Aligne Gabriella Corduroy Dress
En Saison Berenger Long Sleeve Wrap Cotton Shirtdress
AYR The Deepest End Dress
For Holiday Parties
‘Tis the season for endless holiday soirées. Get into the spirit with festive dresses with smooth velvet, lustrous satin, and shimmering sequins. Styles constructed with bold hues and dramatic necklines work just as well. You can rest easy—your dress will work for you while you sit back and indulge in champagne and hors d’oeuvres.
Lioness Field of Dreams Long Sleeve Maxi Dress
PatBO Sequin Keyhole Cutout Maxi Dress
Bardot Verona Sequin Long Sleeve Maxi Dress
Sabina Musáyev Carry Tiered Belted Metallic Dress
Good American Velvet Exec Blazer Dress
AFRM Kay Power Mesh Maxi Dress
Lovers and Friends Simone Dress
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