9 super easy ways to wear dresses in the winter and not freeze

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Wearing dresses in winter is typically not the go-to due to cold weather, but I have rounded up some style tips on how to change that! When you are strategic with layers and/or accessories, you can make your dresses warmer and way more comfortable to wear during winter.

If you want to get the most of our dresses year round, read on to get inspired on how to make your dresses work for you. Yes, you can stay warm and chic even while bundled up!

9 STYLE TIPS TO WEARING DRESSES IN WINTER AND MAKING DRESSES WARMER:

Don’t be afraid to take out your summer dresses! They actually work great for the winter because you can layer very easily!

1. Add Layers and then add more layers

This dress I’m wearing below is a great summer staple – it’s a comfy stretchy cotton and it’s sleeveless – but it also makes a great winter staple because you can layer so much!

I’m wearing a long cardigan and then another long duster jacket over it to add extra warmth.

2. Layer a long sleeve shirt underneath your dress

Adding a long sleeve shirt underneath your dress will turn your short sleeve/sleeveless dress into a winter ready style. The warmth from the sleeves goes a long way and is stylish.

I went an extra step here and layered underneath my dress as well as adding a cardigan over it! If you don’t like the look of the long sleeves under the dress, this is a great way to cover it you can easily add another layer with your jacket!

3. Add outerwear layers on top of your dress

Of course the best part about winter dressing is the cute layers! Put your jackets, coats, sweaters and blazers to good use and layer them on top of your dress. I love how this makes a dress look more elevated.

The winter is the perfect time to bring out all your faux fur! Not only is it warm, it just look so chic!

Don’t forget your vests!

If you know that you won’t be outside for too long or that you’ll be able to run inside quickly, grab your vest! It’s way less bulky but will still keep you warm. I love puffy vests and they go with everything!

Bonus tip: do the same for your kids!

This is definitely a good mom tip as well. My daughters always get too hot when they head anywhere indoors that has heat, so guess who ends up holding all the coats? Yup, mom! So instead of having to deal with that, we’ve made the compromise of wearing a vest and keeping it on which has worked so well!

Dressing your kids for the winter can be tough too so make sure to check out some more cute warm outfit ideas for kids!

4. Replace your tights with fleece lined leggings

You can’t beat leggings. They’re comfy and you can toss anything over them! But don’t be afraid to ditch the leggings in winter! When winter rolls in, it’s time to swap your tights for thicker fleece lined leggings.

They give a really similar look but give so much more warmth! Fleece leggings are great to wear all through the season so it’s a great item that will get a lot of use.

When the cold temps roll around I’m excited to break these leggings out! I love how soft and comfy they are. And the best part, they are easy to wear with boots as you don’t have to worry about things bunching up like you do when you wear jeans.

If you love leggings as much as I do, don’t miss these tips on how to wear winter outfits with leggings.

These leggings are the best ones that I’ve found (and it also have 8,000 five star ratings!)

5. Wear a slip underneath

I love this tip as I feel like it is not as common these days but so helpful! Slips underneath dresses help so that the dress fabric does not stick to your legs, and also adds another layer of warmth in colder months.


A basic slip works great, but if you want to add a little bit more to your dresses, get a slip that fits a bit longer and has a fun hem like this lace hem slip.

6. Layer scarves on top

I love big scarves and they are perfect to add on top of dresses in the winter. You can wear them more classic styled around your neck, or even as a poncho style draped over your shoulders.



I tend to go for more neutral colors for my scarves as they pair so well with most of my winter wardrobe. But don’t be afraid of color! It’s always fun to add a bright pop of color when your jacket and your boots are black.

7. Wear your dress as a tunic and pair with leather leggings or denim

I love turning some of my shorter dresses into a tunic style blouse! It’s a great way to get more use out of items in your closet. Just pair them with your favorite skinny denim or leather leggings for a sleek look.

8. Wear taller boots with your dress

This is for my fellow over the knee boots lovers 🙂 These boots are the best in the winter as they cover most of your leg and are a lot warmer than booties/flats. I also love the look of higher boots with dresses, it feels elevated and stylish.

If you are short like me, find dresses that run on the shorter side so you can still be a little bit of skin between where the dress ends and the boots begin.

One of my pet peeves are over the knee boots that do not stay up! Make sure to find ones that are snug to your legs or have ways of tightening them to your legs. These over the knee boots are my go-to’s. Although they are on the pricey side, but because I can wear them year after year, the price per wear is actually quite good!

9. Wear a pullover sweater or sweatshirt on top of your dress

This is so fun as it turns your dress into a skirt! Just pair a cute pullover sweater or sweatshirt on top of your dress and you have a whole new look! You can use this method for day or night outfits.

It almost feels like you double your wardrobe when you do this!

A tip to keep your sweater tucked in is to use a belt higher up on your waist and then tuck your sweater into it! I’ve also heard wearing a sports bra over your dress (obviously if your dress doesn’t have too much fabric on top) works great to tuck your sweater into as well.

STYLE INSPIRATION FOR WEARING DRESSES IN WINTER

If you need some more style inspiration, I’ve rounded up some of the best inspo around the internet!

These lovely ladies have so much style and I’m bookmarking this page just so I can come back to it when I’m getting dressed and need some ideas. I recommend you do the same, or you can pin the images to Pinterest as well!

STYLING A SWEATER ON TOP OF DRESS:

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LAYERING OUTERWEAR OVER A DRESS:

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STYLING A DRESS WITH TALL/OVER THE KNEE BOOTS:

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STYLING DRESSES OVER JEANS:

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STYLING DRESSES OVER LEGGINGS:

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STYLING A SCARF WITH A DRESS:

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Need more cold weather style tips?

Winter Capsule wardrobe essentials for moms

How to wear leggings in the winter

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