Stay Warm in Dresses: Winter Style Hacks 2025

Want to know how to style a dress for winter 2025? I’m revealing the secrets to confidently wearing dresses even when it’s cold! Plus, learn how to adapt your favorite summer dress for winter, allowing you to enjoy them all year long!

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How To Wear A Dress In Winter 101

Winter’s chill doesn’t mean dresses are off-limits! While it might not be your first thought, many winter holidays and events call for dressing up. I’m sharing my top tips on how to rock a dress, even when it’s freezing outside. Get ready to embrace winter dresses!

Prepare to embrace dresses throughout the entire winter season with this updated style guide. If your winter wardrobe currently lacks dresses, get ready to add some essential pieces. 

Is it OK to wear a dress in the winter?

Yes, dresses are perfect for winter! Opt for winter-ready styles like sweater dresses. You can even adapt your summer dresses for colder weather. Choose suitable styles and add warm layers, tights, and boots for a cozy and stylish winter look.

Don’t let cooler weather cramp your style! Discover chic dress options perfect for staying warm and looking fabulous. Keep reading for the latest trends!

Opt For A Sweater Dress

Achieve the Style:

The ideal way to wear a dress during winter is to choose a winter-ready style, such as a knit, ribbed, or sweater dress. Sweater dresses remain a classic cold-weather choice, making them a reliable winter wardrobe essential.

The market offers a vast selection of sweater dresses. Explore mini, midi, or maxi lengths. Choose from luxurious wool, soft cashmere, or breathable cotton fabrics.

For this ensemble, I paired a ribbed knit midi dress with a fitted black cardigan. This adds depth and an extra layer of warmth. The dress falls at my knees, so I chose these stunning Poppy Barley Toujours knee-high boots to complete the look and keep my legs warm.

How To Wear A Summer Dress in Winter

Want to wear your favorite summer dresses even in winter? (Or any time of year!) Here’s my advice on how to make it work in 2025!

Tip 1: Layer Over

Achieve the Style:

This ensemble features a timeless floral midi dress, perfect for spring and summer. It boasts charming flouncy sleeves and a feminine silhouette (originally from Evernew, now sold out, but I’ve included similar options above). By adding a cozy sweater, this summer dress effortlessly transitions into a stylish outfit suitable for both fall and winter.

Achieve this style effortlessly. Just layer a cozy knit sweater over a midi summer dress. Use an ‘invisible’ belt to tuck it in and define your waist. This gives the sweater a more flattering silhouette. (Discover more tips on styling sweaters over dresses here).

Outerwear and footwear are key! I then draped my Quince leather jacket over my shoulders. I also added knee-high boots and a black shoulder bag to finish the outfit.

Stay warm and stylish this winter with the right outerwear. A jacket, wool coat, or trench coat instantly elevates your look. Transform your summer dresses into cold-weather outfits by layering them with these essential pieces.

Tip 2: Layer Under

Achieve the Style:

Mastering winter dress style hinges on layering. Layering over dresses extends their use beyond summer. But remember, in winter, under-layering is key too.

Sleeveless or slip dresses are ideal for layering. Try a thin, long-sleeved top (similar to mine) or a light turtleneck underneath. A lighter top prevents bulkiness and keeps the dress looking stylish.

For this outfit idea, I layered a coordinating long-sleeve top beneath my sleek black slip dress. This gives the dress a long-sleeved appearance. Chelsea boots are ideal with maxi dresses during winter. Alternatively, consider heeled ankle boots or combat boots for a different vibe.

Boost your warmth! Add a vest or jacket as an additional insulating layer. 

Tip 3: Opt For Tights

Need a fresh winter dress style? Consider tights! Opaque tights or thick pantyhose are a reliable way to stay warm and stylish with your favorite dresses.

Winter dresses look fantastic with tights, especially shorter styles. When choosing tights for a mini or midi dress, ensure they enhance your outfit. Sheer tights work well with some dresses. However, for ultimate warmth, consider opaque, fleece-lined tights. They’ll keep your legs cozy and stylish. 

Even with longer dresses, tights are a great choice. For extra warmth under a long dress, consider thermal tights or leggings. Pair them with knee-high boots for added coverage and a stylish, layered look.

Tip 4: Tall Boots Are Your Friend

Achieve the Style:

Transform your summer dresses for winter by swapping sneakers and ankle boots for knee-high boots. These stylish, taller boots instantly winterize any dress and are a top fashion trend. It’s a perfect way to stay chic and stylish when the temperature drops.

For comfortable everyday wear in 2025, consider flat boots, block-heeled boots, or stylish knee-high cowboy boots. These are ideal for long walks and casual settings. Elevate your look with high-heeled, pointed-toe boots in luxurious materials like leather, suede, or embossed leather for dressier occasions.

For this ensemble, I chose black leather knee-high boots. These boots create a striking contrast with the floral summer dress. This contrast effectively transitions the dress into a more winter-appropriate style.

Tip 5: Avoid Neon & Summer Fabrics

Don’t pack away your beloved summer dresses just yet! You can definitely wear them in winter. However, some dresses are better suited than others. Here are my best tips for selecting the perfect summer dress for winter wear:

Stay away from overtly bright colors and tropical prints: you’ll avoid looking out of season.

Instead, choose neutral hues and subtle floral patterns: these look better in the colder months. You can still wear light colors, like white and cream, by intermixing them with dark tones or suede and leather accessories.

Avoid sheer, crochet, linen, and cotton gauze dresses: these breezy fabrics won’t keep you warm in cold weather. Any cover-up dresses or sundresses that look like they should be worn on vacation or at the beach are a no-no. 

If your summer dress meets these standards, it’s perfect for winter wear!

What to wear with a dress to not be cold?

Staying warm in a dress during winter is achievable! Here’s how to beat the cold:

layer a warm knit sweater or cardigan over your dress

wear tights under your dress – fleece-lined or thick tights are best

wear a long sleeve top or thin turtleneck under your dress

add warm outerwear like a shearling-lined leather jacket, long wool coat, or trench coat

wear ankle boots, knee-high boots, or over-the-knee boots

I trust you found these winter dress styling tips helpful. This guide proves you can confidently wear dresses throughout the winter season with smart layering. (And, importantly, stay cozy!)

Don’t pack away your summer dresses just yet! Give them a fresh look for fall and winter. You’ll be amazed at how easily they blend with your cooler-weather clothes.