How to Wear Dresses During Winter for Warmth & Comfort

I bet that when you think about your favorite winter outfits, your mind doesn’t immediately go to dresses, does it? During chilly winter days, we typically want to bundle up to stay warm and feel cozy. And that’s totally normal! But if you want to change it up a bit…a dress can actually be a beautiful (and warm) winter outfit. With a bit of creativity and strategic layering, you can actually wear dresses in colder months without feeling cold. In this post, I’m sharing practical tips on how to wear dresses during winter.

How to Wear Dresses During Winter

Add Layers

The easiest way to wear dresses in cold weather is to add layers. Whether that’s a long sleeve tee under a sleeveless dress or a fabulous wool coat…adding a layer instantly adds warmth. I personally love to wear a dress with a gorgeous faux fur coat or jacket over my dresses. The teddy coat I’m wearing above is the perfect example and is super warm! If it’s not too cold where you live, you could wear a leather jacket, cargo jacket, blazer, duster, etc.

Find even more outfit ideas with this gorgeous teddy coat here.

Add A Scarf

Don’t forget accessories! You can add cute winter accessories that add style and help you stay warm. Adding a scarf around your neck is an easy traditional way to add warmth. But you could also wear your scarf as a wrap if you need more warmth around your upper body. This is a great tip for a winter wedding if you need a little extra coverage and warmth.

Find 10 ways to style your blanket scarf here…this is an oldie, but a goodie!

Wear Leggings

Wearing leggings under your dress is another quick way to add warmth. If you’re wearing a long maxi dress, you can get away with any kind of leggings…in which case, I’d opt for some super warm fleece-lined leggings. But with shorter dresses like minis and midis, you’ll want to make sure whatever leggings you’re wearing are complimentary to your dress. You can usually get away with a nice pair of black leggings under most of your dresses. You could also try tights, but they won’t be quite as warm.

If you’re curious about what the difference between leggings and tights is, I share everything you need to know here.

Wear Taller Boots

One item you should already have in your winter wardrobe is a pair of tall boots. They can be knee-high boots, over-the-knee boots, or a taller mid-calf style boot. Having a taller pair of boots with your dress covers more of your legs and therefore keeps you warmer.

I shared 12 ways to wear boots with a dress here in case you’re looking for some dress and boots outfit inspo!

Wear A Slip

When you think of winter dressing, you probably don’t think about slips. Slips are traditionally worn with those lightweight, sheer fabrics not typically worn during the winter. But wearing a slip underneath your dress during the winter can also help keep you warm! Make sure your slip is in your skin tone or neutral colors to avoid being able to see it through your dress.

Winter Dress Outfits

Mini Dress & Tall Boots

If you’re a regular reader or subscriber, you’ve seen this outfit before. I shot it on our recent trip to Texas and just LOVE it! I’ve gotten questions about how to wear a short dress in winter and this is exactly how I’d do it. If you’re worried about your legs getting cold, you can wear a pair of leggings or tights under the dress. But the taller boots and the big teddy coat really help keep you warm.

Black Dress & Teddy Coat

Next up is another outfit from my Texas trip and definitely a sexy option you can pull out for those winter date nights! The longer length and ribbed knit fabric of this dress and the taller mid-calf boots help keep me warm. I added a teddy coat and I’m ready for date night. If you’re worried about your legs being cold, again…just add leggings or tights! If you need even more warmth, try adding an additional piece of outerwear or swapping the teddy coat for a cashmere or wool blend coat.

Sweater Dress w/ Tall Boots & Trench Coat

How to style a midi dress in winter is another commonly asked question on the blog and social so let’s dive in… In this look, I’m wearing a fitted sweater dress with long sleeves, a high neck, and a midi-length. I paired the dress with some tall knee-high boots, so my legs are completely covered. And to complete the look I threw on a gorgeous suede trench coat. This look could be recreated with any midi dress, knee-high boots, and coat you already have in your closet. You can throw this on for pretty much any occasion and look super chic and sophisticated.

Dress with Tights

Next up…wear your dress with a pair of black tights! I went with an all-black look here but you can wear your black tights with pretty much any dress. This BB Dakota dress is shorter but the tights help keep my legs a little warmer. I opted for a faux leather blazer but I could also wear a longer coat for more warmth on my legs. This would be a great outfit to try out with a pair of black fleece-lined leggings too.

Maxi Dress & Tall Boots

You know those summer dresses you feel like you can’t wear during the winter? Well, you can! Want to know my big secret on how to wear a summer dress in winter? Well…just add tall boots! Yep, it’s that simple! You can take your fun floral winter dresses and just add a pair of boots to winterize them. Of course, you’ll then want to throw on a coat, some jewelry, and grab your handbag. But it’s a pretty simple transition. If you’re wearing maxi dresses, you can also add those leggings to keep your legs extra warm!

Maxi Dress with Leggings

Next up is how to wear a maxi dress in the winter! It’s hard to tell in the photo above but I’m wearing this beautiful printed maxi dress by Misa with a pair of snow boots and leggings. The dress has a more sheer bottom, so the leggings really help keep me warm. You could throw a black coat over this for an effortless dinner look and feel cozy, comfy, and warm!

How do you like to style your dresses during winter? Let us know in the comments below!

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