Winter Outfits Are Hard, But Here Are 9 Ways to Wear Dresses This Season

When I used to think of wearing a dress, my brain immediately switched to the thought of summer. Breezy fabrics, colorful prints—you know the exact vibe I’m referring to. Now, my thought process is a little different. I actually enjoy wearing dresses (and have more fun styling them) in the colder months than in the warmer months. Before you call me crazy, just hear me out. You can wear your dresses with stockings or a coat, and a pair of boots always makes a dress look cooler. While retailers put out a great variety of dresses in the summer, it’s the moodier prints and knit versions that come out during the fall and winter that truly capture my heart. To prove that you can indeed wear dresses in the cold, I pulled together a few outfits that will do the explaining for me.

Below, you’ll find nine fashion insiders wearing their best dresses layered up for the colder months. Whether they’re wearing a thick jacket or playing around with tops underneath the dress, they’ve got some great outfit ideas for you below.

Growing up, I always thought puffer jackets couldn’t be styled. But I was surely wrong, and this outfit proves it. Keep warm in your favorite floral dress by adding a long puffer and boots to your look.

If you don’t want to wear layers over your dress, how about under your dress? Nawal layered a turtleneck underneath a very summery dress and put on a pair of stomping boots to add that winter edge.

Not one for leggings or stockings? Try the unconventional route and add a pair of straight-leg jeans underneath. 

Bomber jackets are back, but this time with a more oversize fit. Contrast the loose fit with a fitted dress.

Attending a winter wedding or holiday party? Opt for a velvet number. It’s the best time to pull out the luxe fabric. Add a bedazzled bag for the perfect touch.

The winter weather these days has been up and down, so for the warmer days, you can get away with a simple sweaterdress and boots.

The more sweater, the better! I know sweaterdresses are simple, but try tying another sweater over your shoulders. It acts as an accessory and can provide additional warmth when you get cold.

A trusty leather blazer is something that will always be useful in your arsenal. Throw yours on top of any mini dress this season. If it’s a little too cold out, you can opt for stockings.

Is there a better way to brighten up the dreary winter days than by wearing a dress in a standout color?

Next: I Thrift Almost All My Outfits—Here’s What I Always Look for While Shopping