How To Style Dresses In Winter: 20+ Outfits And Top Tips 2024

Winter and early spring don’t have to signify the end of dress season. In fact, dresses can be a quick and stylish solution that effortlessly glides over any winter blues. They are your wardrobe allies and confidence boosters all year round. However, there’s a small challenge: Wearing a dress when it’s bone-chilling cold can be less than fabulous. Fear not, though, as I’m here to share the ultimate tips on how to style dresses in winter.

In this article, I will to provide you with the essential and only tips you need to wear dresses in winter. Additionally, I’ll showcase outfits to offer you ideas and the necessary inspiration to confidently navigate the chilly season. Because from Hanukkah to Christmas, New Year’s Eve to Valentine’s Day, the coldest months often host the fanciest occasions. I’ll make sure you not only stay warm but also look cute and chic no matter where you’re headed.

You don’t want to read the whole text? I got you!

To ensure you have all the essential information right at your fingertips, I’ve compiled a summary for you. Here, you’ll discover all the necessary tips and ways to style your dresses even in winter. For more detailed insights and outfit inspirations on how to style dresses in winter, continue reading further down in the article.

🧥 Layering is Key:

Embrace layering to stay warm. Pair your dress with a stylish coat, a wool jacket, or a sweater for additional warmth.

🐢 Turtleneck Chic:

Consider wearing a turtleneck under your dress for a stylish and warm ensemble. This not only adds an extra layer of insulation to keep you cozy but also introduces a trendy and sophisticated element to your winter look.

🩰 Opt for Warm Tights or Leggings:

Choose opaque tights or thermal leggings to protect your legs from the chill. This allows you to wear your favorite dresses even in low temperatures without freezing.

👢 Boots as Stylish Accessories:

Opt for over-the-knee, knee-high or mid-calf boots to not only keep your feet warm but also add a fashionable touch to your winter look. This combination works well with various dress lengths.

👗 Cozy Up with Sweater Dresses:

Invest in sweater dresses, which are not only trendy but also offer snug warmth. Pair them with a belt to accentuate the waist and add structure to the outfit.

🧣 Accessorize for the Finishing Touch:

Add hats, scarves, and gloves to complete your winter ensemble. Accessories are not only functional but also add a personal touch to your look.

You want more? Here is a Video for You!

In this video, you’ll delve deeper into essential tips on how to style dresses in winter. Towards the end, you’ll also discover initial ideas and outfit inspirations.

How to Style Dresses in Winter – Tips and Outfits

How to Style Dresses in Winter – Best Outfits to Style

Now that you’re familiar with the tips and techniques for styling dresses in winter, let me provide you with some outfit inspirations. I’m confident there’s something for everyone.

1. Black Ribbed Turtleneck Dress with a Camel Coat

 Winter Dress Outfit
by Pinterest

Effortless chic: Pair our Black Ribbed Turtleneck Dress with a Camel Coat for a timeless winter look. The ribbed texture adds flair, and the camel coat brings classic warmth. Perfect for both city outings and cozy dates, this ensemble strikes the ideal balance between style and comfort.

2. Knit Dress with a Button-up Top and Knee-high Boots

 Knit Dress Winter Outfit
by Pinterest

This ensemble effortlessly blends coziness and fashion-forward flair. The knit dress provides comfort, while the button-up top adds a touch of versatility. Paired with knee-high boots, this outfit becomes a statement of chic winter elegance.

3. Black Mini Dress with Tights and a Black Coat

 Mini Dress Winter Outfit
by Pinterest

This ensemble exudes timeless elegance and warmth. Ideal for a night out or a sophisticated urban look, the classic black-on-black combination makes a bold statement. The look is also a good example of how a scarf not only provides warmth to the outfit but also adds an extra eye-catching element.

4. Ribbed Dress with Tights all Black

 Dress Outfit Winter
by Pinterest

Embrace winter sophistication with a Ribbed Dress paired seamlessly with all-black tights. The ribbed texture adds depth, and the all-black ensemble exudes understated elegance. This look is a versatile canvas, perfect for both casual outings and evening affairs.

5. Black Turtleneck Knit Sweater Dress layered with a Black Blazer and Tights

 Dress Outfit Winter Nights Out
by Pinterest

The snug knit dress provides warmth, while the structured blazer adds a touch of refinement. Paired with tights, this ensemble strikes the perfect balance between comfort and style.

6. Apricot Turtleneck Knit Sweater Dress layered with a Denim Jacket and Tights

 Sweater Dress Winter Outfit
by Pinterest

Infuse your winter wardrobe with a breath of fresh air by donning a White Turtleneck Knit Sweater Dress. Layer this cozy piece with a casual Denim Jacket for a touch of laid-back charm. Complete the ensemble with snug tights, and you’ve achieved a perfect blend of comfort and style. Swap the denim jacket for a coat for additional warmth.

7. Belted Midi Dress with Knee-High Boots

 Midi Dress Winter Outfit
by Pinterest

Elevate your winter style with a Belted Midi Dress paired with knee-high boots. The belted waist adds a touch of sophistication, while the boots provide warmth and a dash of chic flair.

8. Belted Ribbed Midi Dress with a Leather Jacket

 Ribbed Midi Dress Outfit
by Pinterest

Sleek and edgy: Make a statement with a Belted Ribbed Midi Dress adorned with a Leather Jacket. The ribbed texture adds depth, and the belted waist creates a flattering silhouette. Layering with a leather jacket brings an edgy touch, making this ensemble perfect for a night out or a bold daytime look.

9. White Sweater Dress with Brown High-Knee Boots and a Camel Coat

 Sweater Dress Winter Outfit
by Pinterest

The softness of the sweater dress meets the warmth of the camel coat, creating a harmonious blend of comfort and style. The brown high-knee boots add a touch of sophistication, making this ensemble ideal for both casual and more refined winter occasions.

10. Turtleneck under your favorite Summer Dress

 Turtleneck Summer Dress Outfit
by Pinterest

Transform your beloved Summer Dress into a winter-ready masterpiece by adding a cozy Turtleneck underneath. This unexpected pairing not only provides warmth but also breathes new life into your summer wardrobe. The juxtaposition of light and warm fabrics creates a stylish contrast, making it suitable for various winter settings.

11. Turtleneck Sweater unter a Midi Dress

 Turtleneck under Midi Dress Outfit
by Pinterest

This stylish layering not only offers additional warmth but also introduces a dynamic mix of textures. The snug fit of the turtleneck complements the flowing elegance of the midi dress, creating a look that’s both cozy and sophisticated.

You want to discover more ways how to style dresses in winter? Make sure to check out our Pinterest!

How to Style Dresses in Winter – 10 More Outfits for You!

To give you even more inspiration on how to style dresses in winter, here are 10 more outfits for you. They are based on the outfits I’ve shown you above but with slightly different color combinations and shades.

Again, if you want to discover more ways how to style dresses in winter, make sure to check out our Pinterest!

How to Style Dresses in Winter – Tips and Tricks

Warm Upper Body Layering:

Elevate your winter dress ensemble with the allure of layering. Consider a chic coat, whether a timeless trench or a plush faux fur option, transforming your outfit into a winter fashion statement. Add cozy cardigans, be it a chunky knit or tailored wool, draped effortlessly over your dress for warmth and style. Opt for a turtleneck underneath to infuse elegance, peeking out from under sleeveless dresses or enhancing the neckline of long-sleeved numbers.

Stylish Lower Body Layering

Elevate your ensemble by choosing warm tights or thermal leggings, adding a touch of flair with patterns or textures. Step into the spotlight with knee-high or ankle boots, not just as a practical choice for warmth but as stylish companions that effortlessly merge fashion and function. Experiment with different boot heights to complement various dress lengths.

Final Touch with Accessories

Let’s talk about winter accessories – the unsung heroes of warmth and style. Picture this: a chunky scarf, artfully draped or snugly wrapped, stealing the show. Top it off with a cute beanie for that touch of casual chic. And don’t underestimate the power of gloves and statement jewelry! Leather gloves exude sophistication, and bold jewelry turns a simple winter dress into a fashion statement.

Seasonal Adjustment for the Holidays

When adapting your wardrobe for winter, consider not only warmth but also the festive spirit of the season. For special occasions like Christmas, New Year’s Eve, or Valentine’s Day, shift towards festive colors such as pine green, burgundy red, or classic black.

Opt for dresses with winter-friendly textures like velvet or knit to accentuate the seasonal charm. Long evening gowns or midi dresses with elegant details make a stylish choice for celebratory events. Complete the look with sparkling jewelry and accessories that capture the winter magic. Remember, winter fashion is not just functional but also an opportunity for glamorous outfits that reflect the festive mood.

My Thoughts on ‘How to Style Dresses in Winter’

When it comes to winter styling without missing out on style, the key essentials are undoubtedly tights. I believe they add a touch of chic and allure while providing much-needed warmth for those who still want to rock their favorite dresses during the colder months.

Another winter wardrobe must-have is the Sweater Dress. Beyond being warm and snug, it effortlessly combines a sweet and cool style. My girlfriend swears by her Apricot Sweater Dress, praising its irresistibly soft and chic qualities.

So, grab a Sweater Dress, throw on some tights, pair it with ankle boots, and top it off with a coat for that extra layer of warmth – and you’re winter-ready. Let’s get in style!

How to Style Dresses in Winter – Frequently Asked Questions

Have some questions and aren’t sure how to style dresses in winter correctly? Maybe the following questions will help you!

What can you wear with a dress in winter?

Pair a winter dress with warm tights or leggings, knee-high boots, and a stylish coat. Add cozy accessories like a scarf and gloves. Consider layering with a turtleneck for extra warmth. This ensemble ensures both style and comfort in chilly weather.

What do you wear on your legs with a dress in the winter?

In winter, wear warm tights, thermal leggings, or even stylish over-the-knee boots to keep your legs cozy. These additions not only provide insulation but also elevate the overall look of your winter dress ensemble.

How do you style a summer dress for winter?

Style a summer dress for winter with a chunky cardigan, warm tights, and ankle boots. Add a beanie and scarf for coziness. This transforms your summer piece into a chic winter ensemble, perfect for staying stylish and warm in colder weather.

Did you enjoy the ‘How to Style Dresses in Winter’ article? Perhaps the following articles could be interesting for you as well!

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How To Style Chelsea Boots In 2024: 17 Stunning Outfit Ideas For You!

What is your favorite way how to style dresses in winter? Let me know in the comments!

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Tobias Huebner

Hi, I’m Tobias. I love staying active, whether indoors or outdoors, flying drones, and constantly striving for self-improvement. Over the past few months, I’ve dedicated a lot of time to refining my personal style. I’ve come to realize that a good sense of style can significantly impact how you feel and boost your confidence. In my posts here, I share my experiences to help you achieve the same.

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