How To Wear Dresses In The Winter

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 tissue thin turtlenecks 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. And if you want a more sheer look, I really like these fleece lined sheer tights.

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.

7 Winter Outfits With Dresses

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. You can even add a fleece lined legging underneath to stay super warm. But to me, this is the perfect winter dress outfit combination: a midi dress and knee-high boots. I love this color and texture combination from Charmed By Camille.

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.

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!

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.

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.

Add Suede Boots

Take any seasonally appropriate dress and add a good suede knee high boot. This even takes those early fall dresses into winter. You can do this with a mini and add tights if it’s cold out, or style it with a midi or even a maxi! If your dress isn’t showing off any skin when wearing your boot, you can even throw on full on leggings underneath for ultimate warmth.

Add A Long Coat

Stay warm in a super long coat. Or in this case of 9 to 5 Chic, a long vest! This is great for an added layer of warmth but it also helps to keep your legs warm. You don’t have to wear fleece lined tights if you’re just going to be out in the elements for a few minutes. A long coat solves that problem!

Add A Third Piece

I think this trick is overlooked a lot in the winter. And it’s adding a third piece like a blazer or moto jacket or any light jacket to your outfit that goes UNDER your big long coat. This is the perfect way to add a layer to your outfit for warmth and also to add some interest and dimension to your look. But then you can easily throw your big wool coat over this to stay warm.

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