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20 Sweater-Weather Dresses that Are Equal Parts Chic and Weather-Appropriate

  • Writer: Qui Joacin
    Qui Joacin
  • Dec 20, 2022
  • 5 min read

Town & Country - Just because it's cold out doesn't mean you have to relinquish your sense of style until temperatures top 40 again. In fact, some would says that the best outfit opportunities lie within your ability to layer, and that goes far beyond just jeans and sweaters either. Dresses are your friends year round, even in the most frigid of weather. Think about the options: sure you probably can't ditch tights, but there are lush knits, velvets, and heavy jerseys galore to tide you over to spring. From a-line dresses, to even some minis, here are the best dresses to wear this winter.

1. Winter White
Vince
Vince Long Sleeve Rib Alpaca & Merino Wool Blend Sweater Dress

Now 60% off

If you ask me, winter white almost always looks stunning. Bright but still neutral, the warm-yet-soft hue lights up the complexion and really allows you to create interest with texture. A buttery pair of tobacco suede boots with this dress? Divine. I'd opt for a knee boot to play with layering proportions and create a long line.

2. Comfy Chic
Wyeth
Presidio Knit Dress

This is the kind of knit frock that works just as well lounging around the house as it does out and about. All you need to add are some accessories—like a chunky vest for example. The deep V and side slit add sex appeal, but the collar and balloon sleeves add polish. All you really need is a pair of sculptural earrings and a good cuff and you have yourself a look.

3. Fun Pattern
Proenza Schouler
Proenza Schouler Animal Print Cutout Long Sleeve Jersey Wrap Dress

Now 40% off

No matter the time of year, wrap dresses are always supremely flattering. This by Proenza is no exception. Pair with a sleek coat and simple ankle boots for easy impact.

4.LBD
St-Roche
ASTRID DRESS

If you stop me on the street and ask what I'm wearing, more often than not it's something by St. Roche. I have a similar dress in a pink print that I absolutely adore and even on my schlubbiest days, I can swap out my many options of heeled boots and layer a cardigan—and add a hair bow to I have myself a feminine and put-together look in a few minutes flat. Obviously, this task will be even easier with a black dress.

5. Give Some Glitter
Metallic Fit And Flare Maxi Dress + Belt

The key here is the sparkle of this metallic fit-and-flare maxi dress. I'd categorize this as understated wow. The kind of dress that you wear to feel sultry but not overly showy. Grab opaque tights—or sheer depending on your shoe, though I'd go for a velvet platform for extra textural contras—and strut on your merry way. Keep the rest of your accessories minimal.

6. Tartan
The Cher Dress

Consider me a recent convert to Black Watch tartan, but an enthusiastic one nonetheless. The square neckline and the ruched waist of this mini make it extremely flattering, and layerable. Throw on some tights and a chunky pair of cashmere socks, add some loafers and you have yourself a modern take on Cher Horowitz.

7. Perfect Paillettes
'Wynnifred' DressBlack

For the moments when you want to wow but don't necessarily want to show a lot of skin. The paillettes in alternating sizes also make sure that you get oooodles of sparkle.

8. Festive Attire
J.Crew
Smocked puff-sleeve cotton poplin midi dress

Now 62% off

Another lovely and feminine take on festive attire, this one is perhaps a bit dressier. The best part about a tartan like this? You really need not accessorize. Wear a velvet headband and be on your merry way.

9. Editor-Approved
The Somerset Collection by Anthropologie
The Somerset Maxi Dress: Velvet Edition

Speaking of velvet, this maxi-dress is much beloved on the internet in its many seasonal variations. Aside from that? It's also endorsed by T&C contributor, Lauren Hubbard.

10. Date Night Pick
Simon Miller
Espen Off-The-Shoulder Sweaterdress

Now 40% off

For a little skin that's also seasonally appropriate, go for off the shoulder. It's inviting and sexy, without leaving you vulnerable to freeze your tail off.

11. Sleek Sweater Dress
Robin Cashmere Sweater Dress

If there's a sleek winter dress that belongs in your closet, no matter your taste, it's a cashmere sweater dress. The classic silhouette gives ample opportunity to to experiment with color, like this not-too-cool green hue.

12. Any Occasion
Marie Oliver
TESSA TIERED MAXI

Every wardrobe no matter the season must have an easy-wearing, out-the-door dress. This is that dress.

13. Intricate Knit
Dodiee
Tulip cable-knit dress

Dodiee's knits are obsession worthy for a number of reasons, chief among them the fact that they give lift and sculpt.

14. Colorful
Frances Valentine
Monaco Maxi Dress Wool Multi

Now 34% off

In the winter, people tend to stick to a more muted palette, but this dress is proof that you absolutely should not. Vibrant and fun, it's hard to not feel happy just looking at it.

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15. Easy-Wearing
Boden
Crew Neck Jersey Midi Dress

Now 52% off

When it comes to easy every day dresses, no one does it better than Boden. With a classic shape, you can buy this in multiple color-ways and never feel like you're repeating a look. Plus, you can't beat the reasonable pricing.

16. Simple Red
Imogen Dress

There's something about a red dress that turns heads no matter the time of year. With the flattering draping and wrap waist, I'd say this piece by La Ligne is no exception.

17. Cool Cord
Boden
Corduroy Midi Shirt Dress

Now 40% off

There's something just so stylish about a good corduroy dress. This slightly utilitarian number gives structure, without being rigid. Pair with soft knits (like a yummy cashmere scarf) and feminine shoes and you have a perfectly balanced outfit. Or add combat boots for some borrowed-from-the-boys cool-factor.

18. Timeless
Shift dress in faux leather

A good shift dress—like this one in faux leather—is the kind of piece that you can build upon season after season for some killer outfits.

19. Feminine Frills
Chiara
Chiara Dress

Sometimes you want to lean into "girly" with a little frill. This dress balances girlish details with a hint of sheer at the sleeves and neckline. Complement with some lug sole boots for edge.

20. Glitzy
Sezane
Adelma Dress

Ah, the understated glamour of French savoir-faire. Here you have a modest cut with just the daintiest sparkle. It's perfect, for the holidays and beyond.

 
 
 

3 Comments


Larry Page
Larry Page
Apr 24

I’m obsessed with these 8 Ball Jackets from Shop Varsity Jacket. They have that perfect mix of retro and urban flair. Super comfy and really well-made. Everyone keeps asking where I got mine!

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cenebe4473
Apr 24

Go for the bold ride-ready style with a Mens Leather Moto Jacket. Classic cut and modern feel. Shop now at Biker Jacket!

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kadofih795
Apr 24

Stay cozy and classic with the john dutton coat—a fan-favorite now at Western Apparel.

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