21 of the Best Winter Dresses.

21 of the Best Winter Dresses

The weather here in Charleston is really touch and go. One day I’m in my Spring clothes, the next it is frigid and cold or raining. A girl has to be prepared! Last week was beautiful, but who knows what next week will be like.

When it gets cold out, jeans, pants, and fleece-lined leggings are often the default choices to keep your warm, but I will always love a dress. There are plenty of winter dresses that toe the line between stylish and cozy.. some are downright warm! Wear them now to stay warm in cold weather with black tights (I will always maintain that Express makes the best black tights!) and heels or boots. Once spring rolls around, ditch the tights and pair with platform sandals.

21 Best Winter Dresses.

Let’s get into a few of my personal favorites! There are so many cute winter dresses to wear all winter long (though most will transition to spring or at the very least, fall!).

Free People Lennon Dress

This is such a good dress, and could pass for Ulla Johnson. I would style it with brown (camel or cognac) high boots. This is one of my favorite winter casual dresses. It would also look great styled under a neutral cable knit cardigan.

The Drop Women’s Renata Rib Midi Dress

Your perfect classic knit sweater dress, at a great price point. Sweater dresses are so great for winter. You can layer them over/under other pieces for added warmth (think: over a thin black turtleneck or a collared shirt, under a chunky knit or oversized blazer). Just add tights and boots or keep things casual with sneakers.

Z Supply Selena Dress

This is your classic black, wear-it-year-round maxi dress. In the spring or summer, wear it with sandals. While it’s still chilly… black tights and platforms, tall boots in a color that contrasts (I’d wear with my green Loeffler Goldy boots)

La Ligne Eleanor Dress

I have this in an eggplant purple floral pattern and it’s the best. Just an easy to wear, comfortable dress that always looks good on. La Ligne’s dresses truly are just the best; I always feel so good in them. I love La Ligne for winter party dresses!

Staud Bridget Dress

I love this little winter mini dress as it takes the guesswork out of layering. The perfect length sweater (vest) dress over a shirt dress. So good!

Classic Six Twiggy Dress

This is the best little shift dress. I love it so much. I have it in white and really want the navy. The faux leather is so great too! It’s one of those seasonless pieces you’ll wear all winter long, but it’s especially chic in the winter with tights and platforms. This is one of the best long sleeve winter dresses if you ask me.

Rixo Maddison Checkered Shirt Dress

This dress is chic, chic, chic and very eye catching. You could layer it over a thin black turtleneck (very of the moment) or under a chunky cardigan. Just add knee high boots and you are good to go (and very warm!).

Ganni Puff Sleeve Velvet Maxi Dress

When looking for winter formal dresses, I almost always choose velvet. How pretty is this one? I love the cut, the silhouette, the puff sleeves… it’s just lovely. Velvet really is such a good multi-tasker. It’s elegant and beautiful but also very warm.

Polo Ralph Lauren Striped cotton and wool-blend maxi dress

I am loving this rainbow long sleeve sweater dress. It is knit from a wool blend with linen and cashmere so it’s bound to keep you warm. This is one of my favorite casual winter dresses. I’d style it with my Goldy boots. You could add a lightweight denim jacket to make it more casual, or layer it over a white button down.

Sika Efe Dress

This dress combines colors I wouldn’t usually put together! I love the print + the heavy cotton fabric. I’d wear this with tights and black platform pumps or sandals, and a fun crochet shawl or cable knit cardigan sweater.

Sea Sonia Print Long Sleeve Smocked Dress

I am such a huge fan of Sea’s beautiful dresses and really love this one. The print is stunning and it is a dress you can wear all year long! I like how the site styled it with white boots. I’d probably do something a little more practical like a camel or cognac.

The Drop Women’s Keyla Puff-Sleeve Square-Neck Tiered Midi Dress

I love leopard this time of year – it’s my favorite winter “neutral” print. I think it would work really well with a pop of red and a neutral tall bot. Amazon the Drop has a lot of really great casual winter dresses, at great prices!

La Ligne Francesca Dress

This dress is seasonless, but so gorgeous in colder months. I pair mine with my tall Veronica Beard croc boots (sadly sold out, a pre-pandemic purchase). Layer on a chunky cardigan (in cream or camel) for added warmth.

Ulla Johnson Elli Dress

I will say it again just to drive home my point, Ulla Johnson can do no wrong, especially when it comes to casual winter dresses.. I would wear this dress with tights, a camel suede boot, and a slouchy knit on top. Comfortable and chic.

The Drop Women’s Daksha Cotton Smocked Zipper Detail Dress

I swear I saw a dress JUST like this on the La Ligne website… this is just a really great price! I love all the colors… there are so many good ones (red would be fun right now, white for summer!)

English Factory Mixed Media Pleated Mini Dress

I love this dress; it has such a flirty and preppy vibe! I’d style it with black tights and ankle boots now or with sneakers in the Spring.

The Drop Women’s Suki Rib Midi V-Back Sweater Dress

I love a good sweater dress for winter and this one is a great price plus so cozy. Definitely a good warm winter dress, plus so many ways to style it. I’d wear it with tall boots and tights, and layer it over a thin turtleneck for added warmth.

Winter Dress Outfits

Best Winter Dresses | Maxi Dress + Platforms
Maxi Dress + Platforms

This is a favorite recent outfit, worn in my trip to New York at the beginning of February. It was cooler than usual so I skipped tights but usually I would pair with black opaque tights to stay warm. The dress is Oliphant (use code GRACE15 for 15% off) and the platforms are Stuart Weitzman.

Green maxi dress | Best Winter Dresses
Green Maxi Dress

This is an older post but this Rhode emerald green maxi dress is still a favorite. I wore it with nude pumps in these photos but today I’d pair it with my Loeffler Randall Goldy Knee High Boots, a slouchy bag, and maybe even a chunky cardigan for extra warmth.

Mini Dress, Tights, Platforms | Best Winter Dresses
Mini Dress, Tights, Platforms!

This is a favorite combo right now… it feels very sixties! I paired my beloved Classic Six Twiggy Dress with Sheertex Polka Dot Tights (the best, they do not run or rip!) and fun sky high platforms. Even after owning it for so many years now (I forget when I bought it but it was pre-pandemic!) I am still loving this dress.

Turtleneck Sweater Dress with Tights
Turtleneck Sweater Dress with Tights

This is always easy and effortless. The one from this post is still available (it’s $35 and such a good Amazon find; love the chunky sweater knit). This is an older post; if I were wearing it today I would size up (I’m wearing a medium in the post, I’d size up to a large) for a slouchier fit. Pair it with our favorite black tights and black boots (knee high or over the knee; not riding boots — those are getting put away for now). A hair cut wouldn’t hurt either 😉

Weekend Reading 1.21.23 | La Double J Swing Dress with Tights
La Double J Swing Dress with Tights

I honestly cannot think of a better dress than the La Double J Swing Dress. It is just the best — easy to throw on, and completely seasonless too! Thank me later. I have several in varying silhouettes… mini, midi, short sleeve, long sleeve, etc. This time around I am wearing this one, which might just be my favorite of the bunch. This look is perfect for date night if you ask me!

Weekend Reading 1.14.23 | Long Blazer + Mini Dress
Long Blazer + Mini Dress

Another La Double J dress (I clearly have a problem), this time the mini swing dress! I love this print. I paired it with my favorite long navy blazer and had a little fun with the shoes. Usually I would do black on black but in this case I really went for it with the gold platforms.

Sezane wrap dress | Best Winter Dresses
Wrap Dress + Boots

this is a Sezane wrap dress with (quite old) Stuart Weitzman over-the-knee boots. I love the combination and the clean line (the dress hem covers the top of the boots).

Feather Mini Dress + Tights | Best Winter Dresses
Feather Mini + Tights

This Borgo de Nor number is not going to be for everyone but I love it, and it is one of my favorite winter party dresses. It’s fun now with tights, and will be just as fun come spring and summer with bare legs and a fun sandal.

What are your favorite dresses to wear in the winter?


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  1. m:

    I love every single one of these dresses—especially the sheer navy. Thanks for the roundup!

    2.24.23 Reply
    • grace at the stripe:

      I’m so glad! You are welcome!

      2.24.23 Reply