21 Cute Winter Dress Outfits [Photo Inspiration and Suggestions]

As winter approaches and the weather changes, you’re probably already dreaming of breaking into your stylish winter wardrobe. There are so many different winter outfits that you can wear to express yourself and stay warm! Lucky for you, just because it’s wintertime, it doesn’t mean you have to stop wearing dresses. From casual to formal, there’s a winter dress outfit for every occasion. 

Some winter dresses will need to be paired with coats, jackets, or sweaters to keep you nice and toasty. You’ll probably also need to wear tights or tall boots to keep your legs warm, too. Wearing dresses in the winter may require more of a thought in the “getting ready” phase to ensure optimal warmth!

Dresses can be worn year-round, and we’re here to show you how you can best do so in the winter. Just follow along to see 21 cute winter dress outfits. Without further ado, let’s get into it!

Elegant young woman wearing a dress in a winter day, 21 Cute Winter Dress Outfits [Photo Inspiration and Suggestions]

1. Monochromatic Grays

Fashionable young woman with a cute winder dress outfit and hat is walking on the street.

Go all out with a monochromatic gray color scheme. Black polka dot sheer tights provide a fun pattern to the otherwise solid-colored outfit. 

Polka Dot Tights

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2. Winter Florals

Portrait of a beautiful young woman with a cute winter dress at the doorstep.

While florals are typically worn in the summer months, this dress takes on the challenge of winter florals. It has a lighter color palette and is given a moody feel through the olive green coat.

3. Over-The-Knee Boots

Portrait of beautiful young woman, 20 years old in city downtown, wearing high-end fashion, cute winter dress

Complement your sweater dress with over-the-knee boots. The boots, coat, and handbag all match each other, creating a cohesive look. The ivory dress stands out against the black accessories. 

Black Over-The-Knee Boots

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4. Long Sleeve Blue Dress

Beautiful young woman in a blue winter dress and a long gray vest

A long sleeve blue dress will capture attention during the winter months. It’s a bright color to be worn in the winter months. Tone down the color by pairing it with a gray cardigan and black boots.

5. Red Cardigan And Polka Dot Dress

A crimson red cardigan is an excellent way to brighten up your black and white polka dot winter dress. It will keep you extra warm, too. 

6. Casual Sneakers

Put a casual spin on your dark gray winter dress with white sneakers. This look is something you’ll never regret: it contains style and comfort all in one. 

7. Beige Sweater Dress

A beige sweater dress can easily stand on its own. Complement it with some camel-toned booties and a designer handbag. 

8. Colorful Infinity Scarf

Easily add warmth and a pop of color to your black dress with the help of a colorful infinity scarf. Match it with some burgundy booties. 

Winter Plaid Infinity Scarf

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9. Black Sweater Layer

Stretch the use of your favorite summer dress into the winter months by wearing a black sweater underneath it. 

10. White Turtleneck Layer

Turtlenecks are so underrated. It’s a chic way to turn any dress into a winter dress. Pair the outfit with some classic shiny black Doc Martens and a small black handbag. 

Black Leather Doc Martens

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11. Black Cardigan And Tights

Stay warm by pairing your floral dress with a black cardigan and black tights. Black tights are a classic look and pull the look together. 

12. Brown Hues With Florals

A floral dress carries happiness with it. To give your outfit a winter makeover, pair the dress with other brown clothing like a scarf, coat, tights, and booties. 

13. Black Peacoat

Peacoats are a classic winter wardrobe staple. It has the ability to make any outfit look polished and classy. 

14. Sweater Over Dress

Throw on an oversized sweater over your dress to turn it into a winter outfit. This cozy gray sweater looks ideal with the black silk slip dress. 

15. Beige Complements

Together, ivory and beige are beautiful complements. The ivory sweater dress contains rich texture and pattern while the beige coat and over-the-knee boots finish off the elegant look. 

16. Long Sleeve Semiformal Dress

This long sleeve black dress is perfect for semiformal events. It’s simple yet elegant and can easily be dressed up through jewelry and other accessories. 

Solid Black Long Sleeve Dress

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17. Polka Dot Midi Dress

Make your midi dress last into the winter months with the addition of boots. The consistent pattern on the dress makes it fit for nearly any occasion.

18. Belted Long Floral Dress

Instantly upgrade your long floral dress by adding a belt to the waist. Again, brown suede boots give the dress the perfect touch for the winter.

19. Rugged Bomber Jacket

Give your bright red dress some grunge with the help of a black leather bomber jacket. Black tights and high-heeled booties complete the look with some femininity. 

Leather Bomber Jacket

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20. Burgundy Boots

On an otherwise neutral-colored outfit, burgundy boots provide a gorgeous show of color. It spruces up the brown floral dress in a rather subtle yet electrifying way.

21. Chunky Gray Cardigan

Chunky gray cardigans are a winter wardrobe necessity. It’s perfect for throwing over any dress during the winter months. It even matches the socks poking out of the ankle-high boots.

Let us know in the comment section below which winter dress outfit look you’re going to mimic! Before you go, be sure to take a look at these other style guides:

What Color Shoes To Wear With A Gray Dress

How To Accessorize A Floral Dress [18 Ideas With Pictures]

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