How to Wear Dresses in Winter: 4 trending Outfit Ideas to Stay Warm and Chic

Pinterest LinkedIn Tumblr

How to Wear Dresses in Winter: 4 trending Outfit Ideas to Stay Warm and Chic

Deciding how to wear dresses in winter can seem challenging. While dresses may feel like a staple of warmer weather wardrobes, there are plenty of stylish and practical ways to incorporate them into your cold weather outfits as well. The key is focusing on warmth by layering the right accessories while also keeping your personal style in mind.

How to Wear Dresses in Winter

In this article, we’ll explore four on-trend outfit ideas on how to wear dresses in winter to help you stay both warm and fashionable in your winter dresses this season. We’ll also provide some tips and tricks for pulling together dresses in winter outfits that are practical yet chic. Read on to discover ideas like wearing dresses over pants and shirts, pairing them with tall boots, and more. With the right combinations, wearing dresses in the winter months doesn’t have to be complicated or uncomfortable!

Outfit Idea #1: Dress Over Pants and Long Sleeve Top

One easy way of deciding how to wear dresses in winter is pairing a dress over pants and a long sleeve top. This creates an extra warm layered look that keeps you nice and toasty.

Start by picking out a long sleeve turtleneck or fitted sweater top in a neutral color like black, grey, or white. Make sure it is form-fitting underneath the dress. For the pants, go with something high waisted in a complementary color or pattern. This helps create a streamlined silhouette. Black jeans, leather leggings, or printed trousers all work well.

Next, choose a dress in a winter-appropriate fabric like wool, corduroy, velvet, or cashmere. Slip it over the pants and top for instant style and warmth. Finish this how to wear dresses in winter outfit with boots – either ankle or knee-high – along with wintery accessories like a wool coat, hat, scarf and gloves.

Not only does this layered outfit idea keep you warm enough for winter dress wearing, it also looks incredibly chic! Mixing dressy and casual pieces creates visual interest for a very on-trend vibe.

Outfit Idea #2: Dress with Tall Boots and Tights

If you love wearing dresses in winter but need to stay warm in style, consider tall boots and tights to complete your look.

Choose a knit dress made from awarm material like wool. For extra insulation, look for heavier sweater dresses and jumper styles that have long sleeves. Slip on opaque black tights underneath your dress before zipping up a trusty pair of black over-the-knee boots. Waterproof leather or suede boots with a slight heel look extra polished.

Not only does this dress outfit formula help seal in heat on cold days, but it also gives off an instantly cool vibe. The contrast between the soft, feminine dress and the edgy, winter-ready boots creates visual interest. Finish with a wool overcoat and a bold red lip for a runway-worthy winter outfit!

Outfit Idea #3: Dress, Cardigan and Ankle Boots

For a more casual take on how to wear dresses in winter, try pairing with an oversized cardigan sweater and ankle boots.

Start by picking out a long sleeve sweater dress made from a cozy material like wool. For a modern twist, go for one in a cool color like camel or grey rather than basic black. Next, grab an oversized, slouchy cardigan in a color that complements your dress. Layer it on top, allowing the sweater dress to peak through the sides and bottom for visual interest.

Then, slip into a pair of ankle booties. Choose sueded leather or suede boots in black or brown for a rich wintery vibe. They should hit just above your ankle bone for perfect proportions in relation to the dress and cardigan layers.

Not only is this particular winter dress outfit formula super on-trend, it’s also incredibly comfortable! The oversized cardigan coupled with the ankle boot gives off major “model off duty” vibes for effortlessly chic winter style.

Outfit Idea #4: Sweater Dress and Tall Boots

For the girl on the go who still wants to rock dresses in winter, a sweater dress and tall boots is the perfect streamlined outfit idea.

Choose a body-hugging sweater dress that hits no more than mid-thigh in length. Go for one that clings close to your frame so you can easily layer pieces over it. Opt for a neutral color like ivory, blush pink, black or navy blue for maximum versatility.

Next, layer a longline wool coat over your sweater dress, finishing just below the knee. Choose a color that pops, like camel or red, to brighten up your winter look. Then pull on a trusty pair of black over-the-knee boots – either flat or heeled depending on your preference. Waterproof leather or suede boots work well to chicly beat the winter elements.

Top your look by wrapping a colorful plaid scarf loosely around your neck, letting the fringe hang long. This particular dress and boot outfit combo is both warm enough for winter dress-wearing and incredibly easy to throw together in a hurry!


As you can see, there are many stylish options for incorporating dresses into your winter wardrobe! By focusing on warm materials, strategic layering, and wintery accessories like tights, boots, coats and scarves you can comfortably wear dresses all season long.

The key elements across all of these trending winter dress outfit ideas include:

  • Choosing thicker, insulating fabrics like wool, corduroy and cashmere
  • Layering with form-fitting turtlenecks, tops and leggings underneath
  • Adding coverage and personality with oversized cardigans and coats
  • Keeping warm with opaque tights and boots in leather or suede
  • Accessorizing to tie the full look together with scarves, gloves and hats

With the right combination of pieces, wearing dresses in winter months doesn’t have to sacrifice style or comfort. From office-worthy sheath dresses to casual sweater shift styles, you can adapt any dress during cold snaps.

Keep these four modern outfit ideas in mind when deciding how to wear dresses in winter. With a few small tweaks your favorite feminine frocks can transition beautifully into cozy cold weather style!


What fabrics work best for winter dresses?

The best fabrics for dresses in winter are wool, cashmere, corduroy and velvet. They are thick and insulating to retain warmth even during frigid temps. Jersey knits, sweater knits and flannel also make good dress material options when it’s cold out.

What shoes should you wear with winter dresses?

The top shoes to pair with dresses in winter are leather or suede ankle booties, over-the-knee boots, knee-high boots or riding boots. They seal in warmth and protect your feet from elements like snow or rain. Heels can still work with proper layering underneath.

Does layering really make that much difference for winter dress outfits?

Yes! Layering items like leggings, turtlenecks and slips underneath dresses seals in body heat incredibly well. Then adding extra coverage up top with oversized sweaters, cardigans or coats gives you more insulation. The layering effect helps keep you much warmer overall!

Should you still accessorize winter dress outfits?

Definitely! Hats, gloves, scarves and other seasonal accessories pull a winter dress look together perfectly. They add coverage as well while also providing you with the chance to incorporate some personality into your outfit.

Can you wear dresses in winter as daily outfits, or just for occasions?

You most certainly can incorporate dresses into your daily winter rotation! With the right materials and layers they work just as well for running errands, commuting or wearing to the office, as they do for special events and gatherings during the winter.


Wearing chic dresses in winter months doesn’t have to be complicated or overly uncomfortable. With some simple planning around textures, layers, and accessories, your favorite feminine frocks can seamlessly carry you through the colder seasons in style.

Use the tips outlined in this “how to wear dresses in winter” guide to build outfits that keep you nice and toasty without losing any fashion edge. From leggings and sweaters layered underneath to tall boots and wool coats on top, you have plenty of seasonal style options.

Embrace these modern winter dress outfit ideas for gorgeously warm ensembles! With the right combination of cozy and chic pieces in your winter wardrobe, dresses work beautifully for daily looks and special events alike.


I have been writing about random topics on the internet for over a decade. I am the type of person that knows a lot of random useless stuff and have no problem keeping a conversation or talking to strangers anywhere around the world. Don't be afraid to reach out to me! The opinions and statements expressed herein are not officially endorsed or guaranteed by The content of this article is not guaranteed by, and readers are encouraged to exercise their discretion and verify information independently. Should you have any concerns regarding this content, we kindly ask that you utilize our Comment Box or Contact Us form to bring it to our attention. Please note that this information is not liable for any losses, injuries, or damages incurred. Your understanding and cooperation are greatly appreciated.

Write A Comment

10 + four =