Apr17
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I’ve always loved dresses. And not just in the spring or summer but year-round.
I grew up in Utah, where winters are real. Snow, wind, freezing temperatures, the whole thing. Wearing dresses in winter was normal to me, not something that required a lot of thought. I layered properly, chose the right fabrics, and moved on with my day.
So when people say dresses aren’t practical in winter, I always disagree. They can be just as warm as jeans or pants (sometimes warmer) with a few styling tricks. Wearing dresses in winter comes down to a few key things:
- Layering without adding bulk
- Adding warmth where it matters
- Fabrics that hold heat
Once those pieces are in place, dresses in the winter suddenly become a lot more practical.
How to Wear Dresses in Winter
Add a Turtleneck
If I had to pick one winter layering trick I rely on most, this would be it.
A fitted turtleneck under a dress adds warmth and can make your outfit look even more put together, since layering always looks more intentional.
Try a fitted turtleneck like this one under shirt dresses, sleeveless midi and maxi dresses and even slip dresses. Stick to lightweight knits like merino, ribbed cotton, or thin wool for your turtleneck so everything still layers smoothly.
I also own this ribbed cashmere turtleneck from J.Crew that is a very warm, soft option. A high neck makes a huge difference in cold weather and makes a dress feel winter-appropriate.
Add a Sweater
Layering a sweater over a dress is a no brainer but it can easily look sloppy without the right proportions.
The easiest way to avoid looking frumpy is to make sure that you can still see your waist. Here are a few tricks to do that:
- Pair a cropped sweater over a longer dress.
- Tuck a regular-length sweater to highlight your waistline.
- Belt your sweater to create shape where it might otherwise look loose head to toe.
If you aren’t sure how to tuck a sweater over a dress, you can use a simple hair elastic. Grab the extra fabric in the back and twist it into the elastic, almost like you’re making a ponytail and then tuck the extra fabric underneath. I tied my Frank & Eileen mockneck sweater with an elastic to pair with this maxi from Nordstrom.
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Wear Tights
I don’t overthink tights. I just wear them. Once it’s cold, tights become part of the outfit, even if you can’t see them under a long dress. If I’m wearing a shorter dress, I prefer sheer tights since I think they’re chic and flattering, but for extra warmth you can wear opaque tights (80 denier or more) or even fleece-lined tights when it’s especially cold. I always grab these opaque tights from Nordstrom.
Layer With Coats
Your coat can make or break a winter dress outfit, both in terms of warmth and style. A good rule of thumb is the longer the better. Wool coats that have a bit of structure and hit mid-thigh or longer look the best with dresses. A belted coat not only looks chic but helps keep heat in.
This Scarf Coat from Petite Studio I’m wearing below has taken first place in my coat selection because it’s belted, has an attachable scarf, and works with both long and short dresses.
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Wear Tall Boots for Warmth, Not Just Style
Tall boots aren’t just about aesthetics, they’re functional. When it’s truly cold, tall boots are far far warmer than booties. And even if you can’t see the full length of the boot under maxi dresses, it doesn’t matter. The only thing to keep in mind with tall boots is that if you are pairing them with shorter dresses, make sure you have a bit of a gap between the top of the boot and the hemline.
These Sylvia Knee-High Boots are definitely my most-worn tall boot.
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Consider Fabrics When Shopping
Fabric matters more than almost anything else.
When shopping for winter dresses, look for wool or wool blends, ribbed knits, cashmere or heavier cottons.
Thin fabrics and lightweight jersey materials usually require more layering to work. That doesn’t mean you shouldn’t buy them (or repurpose them from your summer wardrobe), it just means you’ll need to use the tips above to make them work.
6 Winter Outfits with Dresses
If you don’t want to think about it, use these outfit formulas to make it easy to wear dresses in the winter.
1. Midi Dresses + Boots
This is one of my most-worn winter combinations.
A midi dress, tights, knee-high boots, and a coat is simple but chic. Perfect for church, lunch, date night, and everything in between
A few midi dresses I’m eyeing right now:
- Oxblood Knit Swing Dress from Tuckernuck
- Cashmere Slit Midi Dress from Quince
- Faraway Midi Wool Dress
2. Loose Sweater Over Maxi Dress
Layering doesn’t need to feel bulky to work.
Think:
- Turtleneck under a dress
- Sweater over top
- Coat and scarf to finish
Even if you don’t have a cropped sweater, you can make your own like I did with this mockneck sweater (pictured below). I threw it over this FRAME dress.
3. Cozy Sweater Dresses
Sweater dresses are no-brainers in winter and probably what most people think of when scouting out a winter dress.
I wear sweater dresses most often with tights and tall boots, whether the dress is long or short. Ribbed or wool-blend styles like the Vivianne Dress from Tuckernuck are timeless and warm.
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4. Tights With Booties + Belted Coat
If I’m wearing a dress in winter, I’m almost always wearing tights.
Black, charcoal, or dark brown tights pair well with boots and coats, and make dresses feel like a practical choice, not a risky one. I get my tights from Nordstrom.
A statement coat like this one from Petite Studio tops the look perfectly and is it’s own outfit. Throw on booties like my Veronica Beard ones and whatever short sweater dress you need for warmth – I always pull my Tuckernuck sweater dress!
5. Turtleneck Sweater Under Dress
This deserves repeating because it works with so many dresses.
It’s one of the easiest ways to turn a summer dress into a winter outfit without buying anything new. You can throw a fitted turtleneck like this underneath a structured dress like this Sézane mini, or layer a looser sweater, like this Frank & Eileen one, over a dress like the one I’m wearing below (I was shocked by how much I loved this look).
6. Suede Boots + Maxi Dress
Suede boots soften winter outfits and pair especially well with knit dresses and wool coats.
They’re a great option when you want something warm but a little less structured than leather.
The best booties money can buy (IMO), are the Chocolate Suede Margaux Booties. They’re the most versatile shoes in my closet and are comfortable all day, which is rare for booties.
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How to Wear Summer Dresses in Winter
If you don’t want to invest in winter-specific styles and fabric, you can still get a lot of wear out of your summer dresses with a few tweaks.
Tips to wear summer dresses in winter:
- Add a fitted turtleneck or long-sleeve layer
- Layer with sweaters or blazers
- Wear tights and tall boots
- Finish with a substantial coat
I got the navy FRAME dress in the summer during the Nordstrom Sale and threw a sweater over it.
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Final Thought
Wearing dresses in winter has always felt natural to me. Growing up in a cold climate taught me that warmth is about how you layer, not what category your clothes fall into.
When you focus on fabrics, accessories and layering, dresses become one of the most practical and comfortable things you can wear all winter long.
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