When the temperature drops, it might feel tempting to pack away all your beautiful dresses — but don’t.
From maxi dresses to mini party pieces, you can absolutely wear them during the cold months with the right layering tricks.
In this ultimate guide, we’ll show you how to wear dresses in winter without sacrificing warmth or style.
Whether you’re wondering how to wear a summer dress in winter or how to style a sleeveless dress in the winter, this guide covers every type of dress — from velvet, leather, and denim, to formal, shirt, sweater, and slip dresses.
1. How to Wear a Dress in Winter (The Basics)
Layering is key. Start with a warm foundation and build from there.
Thermal tights or leggings are your secret weapon.
Add a turtleneck or long-sleeve top under sleeveless dresses.
Throw on chunky knit sweaters, blazers, or long coats for insulation.
Pair with boots (ankle, knee-high, or over-the-knee) to complete the look.
2. How to Wear a Maxi Dress in Winter
You might think maxi dresses belong to summer, but their long flowy silhouettes make them perfect for layering.
Pair a maxi dress with ankle boots and a wool coat.
Add a chunky scarf and belt for definition.
Try turtlenecks under sleeveless maxi dresses for extra warmth.
3. How to Wear a Summer Dress in Winter
Yes, you can totally rewear your favorite floral summer dresses during winter!
Layer a fitted long-sleeve shirt underneath.
Add opaque tights and ankle boots.
Choose wool blazers or leather jackets to balance light fabrics.
4. How to Wear Short Dresses in Winter
Short dresses can still be cozy and classy with smart pairing.
Wear thick tights or over-the-knee boots.
Add a long trench coat or wool cardigan for balance.
Layer with a turtleneck or fitted knit top underneath for warmth.
5. How to Wear a Sleeveless Dress in Winter
Transform your favorite sleeveless dresses into all-season pieces.
Layer with mock-neck tops, mesh long sleeves, or turtlenecks.
Add blazers or wool coats.
Try sheer tights or leggings for extra comfort.
6. How to Wear a Sweater Dress in Winter
A sweater dress is a winter wardrobe essential.
Style with knee-high boots for a cozy yet elegant vibe.
Cinch the waist with a belt to create shape.
Add tights and a scarf for extra warmth.
7. How to Wear a White Dress in Winter
White isn’t just for summer — it’s snow-season chic.
Pair a white dress with cream or camel coats for a luxe monochrome look.
Add beige boots or gold accessories to warm up the outfit.
8. How to Wear a Black Dress in Winter
A black dress is timeless — perfect for both work and parties.
For casual days, wear it with a denim jacket and ankle boots.
For evening, try sheer tights, a blazer, and statement jewelry.
Add a leather jacket for an edgy look.
9. How to Wear a Sequin Dress in Winter
Shine bright even in the cold season.
Layer with a faux fur jacket or wool wrap coat.
Pair with black tights and pumps or boots.
Keep accessories minimal to let the sequins sparkle.
10. How to Wear a Slip Dress in Winter
Effortless and elegant — slip dresses are surprisingly winter-friendly.
Add a long-sleeve top underneath.
Style with a longline cardigan or leather jacket.
Finish with boots and a wool scarf.
11. How to Wear a Velvet Dress in Winter
Nothing says “luxury” like velvet in winter.
Pair with heeled boots and gold accessories.
Add a structured blazer or trench coat for a polished look.
12. How to Wear a Denim Dress in Winter
Denim dresses are great for layering.
Wear a turtleneck or striped knit underneath.
Add tights and combat boots for a casual chic vibe.
13. How to Wear a Leather Dress in Winter
Edgy and modern, leather dresses look stunning with warm accessories.
Style with long coats and ankle boots.
Pair with sheer tights and gold jewelry for a night out.
14. How to Wear a Formal or Party Dress in Winter
Don’t skip the glam just because it’s cold.
Layer with faux fur wraps, elegant coats, or shawls.
Choose velvet or sequin fabrics for extra warmth and luxury.
Add closed-toe heels and statement earrings.
15. How to Wear Boots with Dresses in Winter
Boots are your best friend for every winter dress look.
Ankle boots for midi and sweater dresses.
Knee-high boots for short or mini dresses.
Combat boots for denim and shirt dresses.
16. How to Wear a Shirt Dress or T-Shirt Dress in Winter
A shirt dress or t-shirt dress is perfect for casual winter days.
Layer with a long cardigan or oversized sweater.
Add tights and boots.
Try a belted waist to define your figure.
17. How to Wear a Red Dress in Winter
Red dresses radiate warmth and confidence in cold weather.
Style with black or nude tights.
Add a black wool coat or white faux fur jacket.
Pair with gold or silver accessories.
18. How to Wear a Shift Dress in Winter
Shift dresses are comfortable yet elegant for the season.
Layer with turtlenecks, tights, and blazers.
Add ankle boots or heeled loafers.
19. How to Wear a Spaghetti Strap Dress in Winter
Spaghetti strap dresses can work in the cold — if styled right.
Wear a fitted turtleneck underneath.
Add a cropped jacket or long wool coat.
Style with high boots and minimal jewelry.
FAQ: How to Wear Dresses in Winter
Q1: Can I wear a sleeveless dress in winter?
Yes! Layer with a turtleneck or fitted knit top and finish with a wool coat.
Q2: What shoes work best with dresses in winter?
Boots — ankle, knee-high, or over-the-knee — add warmth and elevate your look.
Q3: How do I wear a slip dress in winter?
Layer underneath with long sleeves or turtlenecks and pair with boots.
Q4: Can I wear a white or pastel dress in cold weather?
Absolutely. Combine with neutral coats (camel, beige, or gray) for balance.
Q5: What’s the best way to make a dress warmer?
Use thermal tights, long coats, and scarves — layering is key!
