You may think that easy breezy dresses can only be worn in the warm summer months. Newsflash: That couldn’t be further from the truth. The key to comfortably rocking frocks in the winter is choosing designs made with soft, warm fabrics, appropriate silhouettes and rich colors.
17 Low-Key Rich Mom Pieces for Effortless Styling
I’m a pro at winter dress shopping — 90% of my closet is dresses. So naturally, I took my expertise and scoured the internet to find the 17 best winter dresses for any occasion. Whether you’re looking for a casual, everyday frock, have a special event or need something to wear to the office, I found the most flattering, stylish winter dresses that will get you through the rest of the season and become staples in your closet for years to come.
Best Casual Winter Dresses
1. An Instant Classic: A cross between a plush sweater and your favorite cozy blanket, this soft Ofeefan knit dress keeps you warm and flatters your shape no matter where (or how) you decide to wear it — just $39!
2. Bundle Up: No winter closet is complete without a sweater dress (or a few). This one from I.N.C. International Concepts has been a staple in mine all season long — was $80, now just $25!
3. Perfect for Layering: This versatile A&F Mia Vest Midi Dress has quickly risen on the brand’s bestseller list, mainly because it can be worn year-round. For the winter months, wear it over top a skin-tight turtleneck, sheer tights and boots — just $110!
4. New Type of Loungewear: Yes, you can wear dresses to relax! Ditch the leggings for this supremely cozy Lounge Long-Sleeve Maxi Dress from Abercrombie — just $60!
5. Favorite Potential: Nordstrom shoppers rave about how this Free People Jaci Sweater Dress is perfect for the winter because it’s soft, warm and super stylish — was $168, now just $134!
6. T-Shirt Dress, but Make it Winter: Ever wish you could just throw on a T-shirt dress in the middle of February and call it a day? Well, you can, because of this simple style from Keedone. Throw on some tights and a pair of boots with this and you’ll be good to go — was $40, now just $26!
Best Special Occasion Winter Dresses
7. Glimmer in the Night: Sparkles aren’t just reserved for the holiday season! You can still shine all throughout winter when you wear this tasteful Grace Karin sequined dress to any elegant event — just $56!
8. Staple LBD: A little black dress can be worn all year round, but what makes this Abercrombie pick so good for winter is the removable straps and midi length — was $130, now just $78!
9. Black Tie Wedding Vibes: Florals for winter? Absolutely groundbreaking. The key to being season-appropriate is choosing a darker color scheme, and I can’t get enough of this incredible A-line ballgown from Selkie — just $399!
4. Two-in-One: Can’t decide on just one dress? Well, have we got the style for you. This SL Fashions Cape Cocktail dress completely transforms. Wear the cape for a dramatic entrance into your event, then take it off for a sleek transition. Everyone will be in awe — just $139!
5. Timeless Beauty: Yes, this Ieena for Mac Duggal dress is a bit pricey, but between the gorgeous silhouette and ritzy silk fabric, it’s one of those pieces that will never go out of style… and you’ll get a ton of wear out of it — just $498!
6. Something More Affordable: On the other end of the price spectrum, this velvet cocktail dress hugs every curve beautifully and is under $50 — just $45!
Best Office-Appropriate Winter Dresses
1. Tweed, but Make it Cozy: Tweed has a reputation for being stiff, but this design from Jasambac has a sweater-like quality while still being structured enough for office wear. It’s basically the best of both worlds — just $53!
2. Upper East Side Chic: Office attire has never been more fashionable. This modest dress from Cece still has a ton of personality. When wearing it to work, you’re sure to garner dozens of compliments — was $119, now just $57!
3. In Constant Rotation: No one likes to be uncomfortable at the office. The solution? This elevated sweater dress from Faherty. The collared neckline gives it a professional touch — was $198, now just $158!
4. Comfy and Professional: This two-piece Halogen sweater dress gives the illusion of a business suit with its tapered silhouette and button-down design. No one will even guess it’s super plush unless they get really close — was $129, now just $100!
5. Preppy Chic: Preppy styles aren’t just reserved for summer! This BTFBM dress beautifully melds an angular collar with a fit-and-flare silhouette and rich colors for an office-appropriate dress that can be worn throughout the colder months — just $43!
20 Cozy Cardigans to Emulate the Rich Mom Look
See more Us Weekly Shopping
Us Weekly has affiliate partnerships. We receive compensation when you click on a link and make a purchase. Learn more!
