5 Cold-Weather Timeless Dresses (Stay Warm and Elegant All Winter)

When the cold weather sets in, it’s easy to gravitate toward warm sweaters, pants, and coats. However, a thoughtfully chosen dress can be the perfect piece for combining warmth and style – especially when everything else feels bleak and gloomy. From versatile sweater dresses to holiday cocktail dresses, here’s a breakdown of the 5 timeless dress styles that will help you stay cozy and chic throughout the winter season.

5 Cold-Weather Timeless Dresses

1. Sweater Dress

The very best winter dresses are sweater dresses. They’re warm, comfortable and forgiving– and they look great with boots, sneakers, loafers, and flats. I especially love a turtleneck sweater dress (I own this turtleneck Vivianne Dress from Tuckernuck in two colorways). A fitted or slightly oversized turtleneck dress can be easily styled with a belt for a more defined waist or worn loose for a relaxed vibe.

I like pairing a sweater dress with ankle boots or sneakers for a casual look, and to dress it up, I opt for a dark colorway and add tights, booties and a fun jacket. You could also buy a rich shade of plum or forest green and pair it with a wool coat, tall boots, and add a scarf for extra warmth. You can’t go wrong with a cozy sweater dress in any length!

The dress I’m wearing below is the Sandalwood Vivianne Crewneck Dress from Tuckernuck. (I have a size small but should have gotten an XS.) I paired it with a brown leather Madewell belt and tall leather books from Larroude. My coat is the Plaid Bouclé Walker Coat from Nordstrom.

2. Day-to-Night Dress

Since the sun goes down so early in the winter, it’s reasonable to assume you’ll be heading straight to your dinner plans from your afternoon meetings. The best dresses for occasions like this are classic wrap dresses. For a daytime look, pair a relaxed-fit wrap sweater dress with casual ankle boots or flats and minimal jewelry. Transitioning to an evening look is easy: swap in heeled boots, add statement jewelry and layer a sleek trench or leather jacket. A belted sweater dress can elevate your evening style while still keeping you warm.

The wrap dress I’m wearing below is the Long Sleeve Faux Wrap Sweater Dress that’s currently sold out, but this midi length wrap dress from Banana Republic is similar (and honestly cuter!). The tall brown boots are the Annika Pointed Toe Boot, and my studded block heels are the Black Foster Stud Sandals from Tuckernuck.

3. Shirt Dress

A good shirt dress is necessary for every season. In the warm months, I like a linen-blend shirt dress. In the winter, I opt for thicker fabrics like flannel or cotton twill, and layer my dress with tights or leggings for added warmth. Pair with ankle boots for a casual day look or add knee-high boots and a trench coat to elevate the style. If you live in the South like me, you can often get away with wearing this style of dress with ballet flats, sneakers or loafers on warmer days. (You can see how I’ve styled a shirt dress for cooler weather in this reel.) I love this idea for family photos as well – see the rest of my ideas for family photos in this post.

The dress I’m wearing below is the Winetasting Crepe Callahan Shirt Dress from Tuckernuck and the ballet flats are the Blair style from Larroude.

4. Maxi Dress

Maxi dresses aren’t just for summer—they’re perfect for winter, too! Opt for long-sleeve maxi dresses in cozy fabrics like wool, jersey, or heavier knits. Or, take your summer maxi (if the colors lend themselves to winter), layer a chunky cardigan or a longline coat over the dress, and add ankle or knee-high boots to stay warm. I love the recent trend of wearing knee-high boots underneath maxi dresses.

The dress I’m wearing below is the Julia Dress by Livro paired with the same Blair flats from Larroude that I’m wearing above.

5. Holiday dress

Holiday dresses are probably my favorite thing to shop for. I look forward to holiday parties all year long and love having an excuse to wear something a little more bold than usual. For holiday gatherings, choose a dress with a bit of shimmer or texture. Velvet dresses are timelessly elegant and bring warmth along with their luxurious feel. Deep jewel tones—like emerald, ruby, and sapphire—add a festive touch to the look. If you prefer a touch of sparkle, opt for a dress with subtle metallic accents. Complete the outfit with black tights, heels, and statement earrings, and you’ll be ready to celebrate in style while staying comfortable.

See all of my favorite affordable holiday cocktail dresses linked in this blog post. (And if you’re expecting, I have maternity cocktail dresses in this post.)

The black velvet dress I’m wearing below is the Elodie Dress from Tuckernuck. I paired it with Sam Edelman Brit Kitten Heels for a festive look.

Tips for Styling Timeless Dresses in Cold Weather

Layer Wisely

Invest in quality tights to wear under your dresses for extra warmth when pairing with booties or even tall boots. Throw on a long coat or cardigan for even more layering. Lands End makes classic styles that are high quality and well-priced, like this FeatherFree Insulated Diamond Quilted Maxi Coat.

Select Warm Fabrics

Look for dresses in wool, cashmere, or fleece-lined knits. 

Don’t Forget Accessories

Winter accessories like scarves, gloves, and hats not only keep you warm but add style. A sweater dress on its own can look drab but styling it makes it look super chic. I added a belt and coat below to take my tan sweater dress from very basic to very polished. Choose accessories that complement the tones of your dress for a cohesive look.

These timeless cold-weather dresses are beautiful and versatile, helping you easily transition from work to play, day to night, and holiday gatherings. If we have to get through winter, we may as well look good doing it!

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