How To Wear Dresses In The Winter

How To Wear Dresses In The Winter
Photo via Charmed By Camille

I’m guilty of avoiding dresses come winter when the temperatures drop. I get lazy and just throw on jeans or pants and my coziest sweater and call it a day. It’s clear that it’s not my thing because I only have ONE outfit post from the archives of me styling a dress for the winter. So clearly I need to take my own advice here and start getting out of my denim rut!

But in the summertime, I live in dresses, they’re my favorite! I’m determined to change that and this post will help to inspire myself and hopefully you, to wear more dresses this winter. Oh, and still stay warm!

How To Wear Dresses In Winter

There’s definitely an art to wearing dresses in the colder months. You want to stay warm which usually means more layers. But you also don’t want to look like a hobo. Here are a few things to try to stay warm, be stylish and still get some use out of your dresses.

Add A Turtleneck

A turtleneck layered under a dress can be a great way to take your year round dress (leave the summer dresses in the closet people!) into colder months. Definitely choose a more tissue-thin turtleneck or at least a fitted turtleneck. It helps to avoid bulk when layering. I love these from J.Crew. Great to layer under a slip dress, or any sleeveless dress you have.

Fleece Lined Tights

I discovered fleece-lined tights a few years back before heading to NYFW and it was a game-changer. They’re the coziest, warmest things ever. They help to keep your legs nice and warm while you’re able to rock your favorite shorter dresses. Even if you’re planning to wear a longer dress with knee-high boots, choose fleece-lined tights to wear underneath it all so you can stay warm.

Layer With Coats

Obviously, you want to make sure you have a great long coat to layer over your dress. A wool coat is a solid choice to keep you warm and look put together. Coats can be a part of the entire look too, so don’t overlook this when putting your ensemble together.

Rock Those Boots

Now’s the time to pull out all the boots you have. Go for knee high or over the knee for an extra layer and more coverage. They also look great with midi lengths too. But you can also grab your favorite ankle bootie or Chelsea boot as they pair perfectly with winter dresses.

5 Winter Outfits With Dresses

How To Wear Dresses In The Winter

Midi Dresses + Boots

A long sleeve midi dress will help to keep you warm in the winter. Plus, adding boots is always a smart idea. Love this color combo and texture combo from Charmed By Camille.

Photo via Charmed By Camille

How To Wear Dresses In The Winter

All The Layers

This outfit encompasses ALL the layers. A thin turtleneck, a light jacket, a scarf, booties and probably tights too. It’s layered, and polished, without looking bulky. By keeping your fabrics in mind, you can really layer and look great while staying warm.

Photo via Gal Meets Glam

How To Wear Dresses In The Winter

Cozy Sweater Dresses

If you don’t want to add a bunch of layers, be sure to choose a really cozy sweater dress for the winter. You can even stay warm by adding a thin long sleeve underneath (I do this with my sweaters sometimes). And don’t forget the knee high boots!

Photo via Glitter and Gingham


All The Tights

My fleece-lined tights are just the greatest thing for winter layers. Pair them with all your dresses and skirts to stay warm and look polished. Whether you see the tights or not, I can’t recommend them enough for staying warm under dresses.

See The Post

Layer A Turtleneck

Layer A Turtleneck

The best way to add a layer, texture and some style to your winter dresses is to add a turtleneck underneath. Be sure to choose fitted ones so they don’t add too much bulk.

Photo via Fashion Me Now →

Jessica is an Atlanta life and style blogger. Aiming to bring practical tips to your every day life. Tips that you can easily tackle and make your life feel just a tad more 'put-together'.

Leave a Comment


  1. 2.10.20
    Karly said:

    This is great outfit inspiration! Like you, I usually just reach for jeans and a top/sweater this time of year. But, since winter isn’t anywhere near finished here in Wisconsin it would be nice to have a few more options in my closet!


    • 2.10.20
      Jessica said:

      I need to branch out. But I think I really need some good brown leather knee high boots like Camille has!

  2. 2.10.20
    Jennifer said:

    Great tips! I definitely have to keep these tips in mind when I wear a dress during the cold season. 🙂

  3. 2.10.20
    Laura Leigh said:

    LOVE that look of Julia’s! It’s been one of my favorites for years – have several screenshots on my phone – that obsessed hahah. Such a great post lady!

    xo Laura Leigh

    • 2.10.20
      Jessica said:

      It’s a good layered look for sure. Need to recreate it!