20 Style Tips On How To Wear Dresses In The Winter While Staying Warm

Just because it’s freezing cold outside doesn’t mean you have to hide all of your dresses away until the temperature goes up a little bit. Dresses can be worn even in the middle of the winter, and all it takes to make them cozy enough is a little bit of layering knowledge. In fact, you SHOULD wear your dresses in the winter. They have the potential to look really adorable and stylish!

In order to make dresses appropriate for winter, you have to have some fashion basics: leggings, tights, boots, thick socks, cardigans, and scarves. You want to look cute, but you also don’t want to freeze your butt off. It’s not worth it! If you’re unsure of how to make your summer dress work for the next few cold months, here are 20 style tips on how to wear dresses in the winter: 

 

1. Pair your lacy white summer dress with a leather jacket or blazer, black tights, and black booties. 

how to wear a dress in winter

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2. On warmer days, just add a scarf and high boots to a long-sleeved dress. 

how to wear a dress in winter

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3. Add as many layers as possible: a chic hat, a jean jacket, a cardigan, a coat, a scarf, and high socks. Cozy! 

how to wear a dress in winter

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4. Wear your dress over a chambray shirt and add tights, ankle boots, and a puffy vest. 

how to wear a dress in winter

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5. Add pretty tights and lace-up boots. 

how to wear a dress in winter

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6. Add a long cardigan, chunky knit scarf, tights, and combat boots. You can even add cute knit socks for added warmth. 

how to wear a dress in winter

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7. Wear your dress with a scarf, tights, and thigh-high boots. It’s almost like wearing pants because so much of your legs will be covered! 

how to wear a dress in winter

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8. Stay warm in a denim jacket, pretty tights, and ankle boots. 

how to wear a dress in winter

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9. Cinch your waist in by adding a belt over your cardigan. 

how to wear a dress in winter

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10. If you don’t want to wear tights, wear thigh-high socks under your high boots. It looks cute and will keep you warm. 

how to wear a dress in winter

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11. Wear a fitted sweater over your dress, and pop the collar out. This is a cute and easy preppy look. 

how to wear a dress in winter

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12. Wear your sleeveless summer shift dress over a button down shirt with tights. Add a belt to make the look less bulky. 

how to wear a dress in winter

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13. If you want to look a little more professional, add a cropped blazer. 

how to wear a dress in winter

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14. Layer with a hoodie, scarf, and ankle boots for a casual vibe that’s still really cute. 

how to wear a dress in winter

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15. A super basic and easy way to wear your sundress in the winter is to add a long cardigan, a chunky knit scarf, tights and ankle boots. 

how to wear a dress in winter

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16. Wear a sweater over your dress to make it look like a skirt, then add high boots and knee socks. 

how to wear a dress in winter

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17. Patterned tights look so pretty with a dress and a cardigan. Add heels to look more dressed up. 

how to wear a dress in winter

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18. You can even wear a strapless dress! Put it over tights and a button down shirt. 

how to wear a dress in winter

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19. Layer socks over knit tights and add lots of texture with a lace blazer. 

how to wear a dress in winter

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20. Adding a fur vest will keep you a little extra warm. Put it over another layer for added warmth. 

how to wear a dress in winter

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Which of these outfits is your favorite? How do you wear dresses in the winter? What kind of style tips do you want to see? Tell me in the comments.

You can follow the author, Jessica Booth, on Twitter or Instagram.

 

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  • Suzi

    Thank you for this. I LOVE wearing dresses in summer and seriously grieve winter when I have to cover up so much!

  • Looks like an old school type of girl. Well nothing wrong with that but sometimes you need to embrace this kind of fashion because we are now living in a new generation.

  • As is the norm with all things that they change over time so does fashion, and now a major part of fashion are the accessories we carry. A recent necessity which has been added to today fashion world Origins winter cambric dresses shawl collection

  • Anna

    I swear this is for like Arizona weather winters! I would know, I lived in both Ohio and Arizona. I wouldn’t wear ANYTHING like those outfits in Ohio winters! Lol these are so perfect for an Arizona or California winter though. Anyways, this is super cute 🙂 maybe not winter in most places, but fall outfits for sure!

  • This is really nice collection. I appreciate your efforts. Thanks for sharing.

  • Sarah

    Have you ever been in a Canadian winter? are you for real?

    • Kate

      I live in Vermont and these could all work IF you make sure those tights are well and truly thick. (obviously you need a winter coat, too.) You really need 100% opaque wool tights or fleece-lined tights. Uniqlo or YesStyle is a good place to look (apparently Asia has a better sense of what “opaque” means and how not to freeze during winter in a skirt.)

    • amberhalvorsen

      I’m glad I wasn’t the only one wondering about this. I was hoping they would suggest actual sustainable options. But I’m thinking maybe I’ll layer like three pairs of leggings or something.