Here’s How to Wear Dresses in the Winter While Staying Warm and Cozy

Like many of you, my jam-packed schedule means that I’m often running a bit short on time. This means that half the time I get ready, I’m drawn to outfits that are easy to put together and don’t take much thought. That’s where dresses come in handy.

Dresses are convenient to wear because they’re such a breeze to style. They’re also really comfortable and leave you with a polished and put-together look (even when you don’t feel that way.)

There’s no denying that dresses are one of the best spring, summer, and fall outfit options, but I’m here to show you that they can also be worn throughout the winter season.

Although cold temperatures and potentially snowy conditions may make it seem difficult to wear dresses, it’s definitely possible if you put just a little bit of effort into your look. I’ve found a handful of ways to stay warm and cozy when styling dresses in the colder months, and I’m sharing those ideas below.

Here, you’ll find everything you need to consider when wearing dresses in the winter, as well as easy to replicate outfit ideas to try this season.

How to Wear Dresses in Winter

Swap heels for boots or sneakers.

Opting for warmer shoes might seem like a small swap, but it can make a really big difference in how toasty you feel when wearing a dress in the cold weather. Reach for shoes like combat boots, over-the-knee boots, or just a simple pair of ankle booties.

If you live somewhere with mild winter temperatures, even a pair of white sneakers might be enough to ensure you stay warm.

Focus on layers.

Perhaps the most obvious way to stay warm while wearing a dress in the winter? Layering up.

Use this season as an opportunity to really “style” your outfits. For example, you could add an oversized wool scarf over your dress or slip into a cute trench coat. You can also wear a shirt or a light turtleneck underneath a dress when it’s extra chilly outside.

Wear tights and tall boots.

Don’t underestimate wearing a dress with tights. Not only will it keep your legs covered, but it can also make a basic outfit feel more “dressed up” and special. Plus, tights are a winter wardrobe staple that can be worn with skirts as well.

Opt for a sweater dress.

The material of the dress you pick will certainly come into play when styling it in the winter. Use your common sense here and reach for pieces that are made with thicker fabrics, like a knit dress or wool find rather than something thin.

Add a puffer vest or coat.

When you’re dealing with particularly cold weather, there’s sometimes no other option than to resort to layering with a puffer coat or vest. While a puffer might not be your first coat of choice, it can actually look really chic when styled with a dress.

10 Winter Dress Outfits

Dress + Knee-High Boots

One of the best ways to wear shorter dresses during the winter is by pairing them with knee-high boots. Taller boots are certainly on trend right now, and like I mentioned above, they’re also a really practical shoe choice during the cool season.

Even if knee-high boots aren’t your thing, there are plenty of other stylish winter boots for women.

Dress + Knee-High Boots
Dress + Tights + Coat

When styling a dress in the winter, one of the most important factors to consider is how you’ll keep your legs warm. An easy way to do that is by wearing tights underneath. I’d recommend looking for fleece lined tights, which are thicker (and cozier) than standard tights.

Pairing tights with a dress and a wool coat makes for the perfect winter date night outfit—just don’t forget to wrap a scarf around your neck for added comfort.

How to Wear Dresses in Winter
Photo: @Cal L
Dress + Trench Coat

I always joke that my “fall uniform” is a combo of leather leggings, a black turtleneck, and a trench coat, but the reality is that this style of coat can be worn throughout all seasons. It’s an incredibly versatile piece that can level up any look.

Try styling a trench coat with a sweater dress and boots for an effortless yet elevated feel. The coat will offer your outfit a mature vibe, and because it’s neutral colored, it will go with pretty much everything you already have in your closet.

How to Wear Dresses in Winter
Photo: @Vanessaajade
Turtleneck + Dress

What if I told you that you could wear some of your favorite summer dresses if you layered appropriately? Well, the good news is that you totally can. Just throw a cashmere sweater or turtleneck on top of your dress to instantly add some warmth.

Long-Sleeve Shirt + Dress

For a less common but equally as chic winter dress outfit idea, incorporate a long-sleeve shirt into your look. Just throw on a shirt (or even a light turtleneck sweater) before you slip into a dress. This is a great way to layer and get use out of dresses without sleeves.

Long-Sleeve Shirt + Dress
Photo: Kelly in the City
Dress + Tights + Cozy Layers

Not to repeat myself but don’t overlook the impact that wearing layers can make. After all, it is the season of bundling up, so lean into that by wearing your favorite winter accessories, like a big scarf, mittens, or even a beanie.

Another good tip is to go with a longer coat that offers more coverage. This is especially important when styling midi dresses in the winter because you want to make sure that your coat and dress aren’t the same length (it can look boxy and unflattering if your coat and dress are too similar in length.)

How to Wear Dresses in Winter
Dress + Puffer Vest

Is snow in the forecast or is it just downright frigid? Pull out your warmest puffer coat or vest and style it over your dress. A vest with faux fur detail would look really cute and seasonally appropriate.

Dress + Puffer Vest | How to Wear Dresses in Winter
Sweater Dress + Oversized Cardigan

This is the outfit I’d suggest on those days when comfort is a priority but you have no choice but to be out and about. Adding an oversized cardigan over a sweater dress can offer visual interest in both textures/fabrics as well as in styles (more form fitted pieced mixed with something more laid back.)

If you don’t love the oversized look and you want something that is more fitted, swap the cardigan out for a cropped sweater.

Sweater Dress + Oversized Cardigan
Photo: @The Cool Hour
Dress + Leather Jacket

The combo of a dress and a black leather jacket makes for one of my favorite winter outfits. It creates such a classic look and would be appropriate to wear for so many occasions. This is also. an outfit that you can likely recreate with pieces you already own—not to mention that a quality leather jacket can provide a good amount of warmth.

Dress + Blazer

Last but certainly not least, pull out your trusted blazer for a timeless and understated look. This outfit is probably most realistic for those of you who live in warmer climates, but it’s also a great option to reach for when you’re transitioning from one season to another.

Which winter dress outfit idea is your favorite? Let me know in the comment section below!

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