As a dress lover who grew up in Wisconsin, I had to quickly figure out how to wear dresses in wintertime (and not freeze my butt off!)
While a good midi sweater dress is always a smart option for cold weather, I’m constantly pulling out my summer dresses and styling them for chilly days.
These are my favorite dresses to wear in the winter (and all seasons) plus tips on how to dress for cold weather while still looking stylish.
How to Dress Warm In Winter (But Still Wear A Dress)
1. Always Wear Tights
First rule of your winter wardrobe is a few pairs of quality tights. They do wonders for trapping in your body heat and keeping your legs warm even in chilly temps.
I usually opt for standard black tights but there’s also these warm fleece lined leggings that look like skin but are much thicker if you need them! This is how to wear summer dresses in winter without your legs freezing off!
2. Layer Sweaters & Vests Over Dresses (Or Under!)
I adore pairing sweaters over skirts and dresses, especially large chunky knits. They’re just so cozy!
And, sometimes if the dress is loose enough, I’ll pop a turtleneck under a dress without sleeves for a layered look that way. Anything to add extra warmth to my torso.
3. Wear Warm Shoes
You lose most of your heat from your head and your feet. It’s important to make sure your toes are nice and toasty if you’re wearing a dress in the winter. Opt for sturdy ankle boots or knew highs with thick socks to keep you warm.
I’ve been jamming on these black boots from Sezane this year. They look rad with winter dresses and are super warm and comfy on the inside.
4. Opt For Longer Coats
Growing up in Wisconsin, I had one rule for the winter: my coat better cover my butt. I swear everything feels a million times colder if your coat does cover your booty, especially when you are wearing dresses.
Opt for long camel coats or puffers that extend enough to keep your whole body warm.
22+ Winter Approved Dresses To Wear In Cold Weather
When it comes to cold weather dresses, I really love anything that’s longer- usually a maxi or midi length dress with long sleeves- to keep me warm in the chilly temps. Here are some of the best winter approved dresses to wear in cold weather.
Tiered Dresses For A Playful Look
A tiered dress is perfect for a fun, dimensional look with extra fabric to keep you warm. Not to mention the best part about dresses is creating easy outfit ideas with just one piece, and the tiers just add a little something.
I’d suggest the Ophelia Tiered Dress from Cupshe (Cupshe is a real winner for me when it comes to winter picks, if you want to see more of their stuff check out 8 Cold Weather Outfits to Wear This Winter).
Sweater Dresses For Everyday
When that first sweep of cold air comes in, all I want to do is curl up with a cup of coffee and take it all in – without the fuss of buttoning up my jeans or even that little extra fabric.
So I’m always on the search for winter outfits to wear when I’m working from home. Of course, if being able to snuggle up in your dress is top priority: the sweater dress is the way to go.
It’s no secret that I love to dress colorfully so this heart patterned is calling my name! So trendy and need very little styling (especially if you’re staying home, avoiding all icy winds and weather).
Oak and Fort took a really cool approach to a sweater dress that I really like this season. Their Half Zip Sweater dress is like a pull over sweater shirt in dress form for sporty vibes!
A turtleneck sweater dress (like this one from Amazon) is a no brainer as a base layer when it comes to dressing cute!
Formal Dresses For Winter Events & Celebrations
As we know, when the winter season rolls around, so do parties and events: Christmas, New Years, sometimes even weddings. My go-tos when shopping for winter wedding guest dresses are: find something that’ll keep you warm, but not too warm for the dance floor. All while, looking elegant throughout the night.
I don’t love buying dresses for a single occasion, so I look for things I know I can dress down or wear to another event. This cashmere turtleneck sweater dress is one of these amazing finds! It can easily be dressed up with heels and nice jewelry or dressed down with a few simple changes!
Dia & Co’s Evalina Midi Dress is another versatile piece for your winter closet. The heavy knit material is a key part to how to wear a dress in winter – functional and fashionable! For more winter formal dresses, I love something like this midi cut sweater dress with cute accents like a puff sleeve that promises that you’ll be the best dressed at any event.
Similarly, this cross front midi dress with a tie belt just gives it a little pizazz. This one can be knotted in the front or the back of the dress, and it comes in sizes up to 28.
Or this Wrap Front mini sweater dress from Abercrombie & Fitch is topping my list of winter dresses. It gives more of a cocktail dress vibe with its shorter length, but the detail of the ribbed sweater material makes this dress more than a simple white dress, and instead a staple piece.
Winter Dress Closet Staples
So when it comes to finding dresses that can stay a closet constant, there are some things to keep in mind: their color palette and their style.
One of my favorite finds has been the Gwen Dress from Sezane- which gives a little bit of a 70s vibe with its all denim design. And is unbelievably comfortable.
While I love color, black is a classic year round color, and easy to create multiple looks from. This fit and flare dress from Old Navy is made of a ribbed material and has a peek-a-boo cut out in the front. Lisa says Gah takes a similar, yet slightly more quirky approach in their Demi Sweater Dress. However, both are definitely for a slightly warmer climate.
If you’re looking for something warm to layer with or wear with a pair of sneakers, this ASOS dress is giving me SKIMS vibes, but if you’re wanting the real SKIMS slip dress dupe, check out these best skims dupes from Whimsy Writer Jafei!
Dresses You Don’t Have to Pack Away
I do love dresses you can bring from one season to the next, and some winter picks from me this year are ones you don’t have to pack away with all your winter sweaters and clothes.
Midi dresses are great for seasonal dresses that need to move from winter to spring. Amazon has a great collection, I love dresses with amazing accents or original details- like this lantern sleeve dress with a drawstring neckline. And of course the Mafalda Midi Dress is a great piece with a cut that can be styled for winter and the cooler spring days.
When it comes to what to wear in winter- I think searching for some pops of color are always a fun way to move out of the gray that we so often feel and see on winter days. That’s why I love the midi Polo Dress from Old Navy.
This dress is a unique spin on the shirt dress and is the colorful dress you need this winter. This Puff Sleeve Dress is another brightly colored dress- and balances the style of a summer dress with the cut of a winter dress. Making this dress a unique must wear winter piece.
I also just love a dress with a great pattern- and in winter, these longer dresses are perfect to keep you warm. The patchwork pattern of the mixed ruched jersey midi dress is perfect for the rich tones of winter and easy to move into a spring style with its floral design. I’m also in love with the Nobody’s Child dress– the beautiful pattern stole my heart, but it has some of the sweetest details- like its buttons and cinched back- that make this dress a must have.
One of my final picks is a fun maxi Dress from ASOS- this really is a fun dress, and a piece that I think will become a winter classic and seasonal favorite.
Shoes To Wear With Winter Dresses
How to wear long dresses in winter, in my book, is just finding warmth in trendy ways. So thank god the rise in 90s and 00s fashion is on its way back so that pairing a midi dress with tall boots looks incredible! (And gives you a Lorelei Gilmore moment!) Personal favorites are the Valentina boots from Nordstrom or the Franco Sarto Sonna boot (I’m in love with the new trend of two toned, wood looking accents on shoes, I think it adds a little pop to an otherwise monochromatic accessory).
For more classic heels lovers, closed toe shoes are an obvious choice when planning for winter events. Platform heels are all the rage right now, and I totally get why. The Romana Platform heel from Simply Be are cute and classy and a great pair for winter dresses for weddings.
Sometimes, of course, even finding a dress that’s just for winter can be a little annoying- or even heartbreaking when I have to tuck away some of my favorite pieces into the back of my closet. Lucky enough there are plenty of wintery finds that you can style across all seasons!
Tell us in the comments your favorite way to uplevel a dress each season!