Our favorite cute winter dresses to brighten up a gray day!

Gray weather getting you down? When the winter blues start sinking in, I find it’s the little things that brighten up my day. Like cute winter dresses! This season we have lot’s of fun options to choose from. Here are my favorite dresses and trends.

Wrapped Up

Cute Winter Dresses - Wrap Dresses  

Source (clockwise from upper right): ASOS Curve, Shabby Apple, Shabby Apple, Macy’s

Take a cue from stylish ladies like Michelle Obama or Kate Middleton and dress yourself up in a classic wrap dress. I like a solid color, so I can layer on my one of my favorite printed scarfs when the temperature dips. More into prints? There’s plenty of choices out there taking inspiration from the original printed wrap dress by Diane von Furstenberg. Did you know her signature wrap dress debuted in 1974, and had sold over 1 million times by 1976?

Winter Brights

Cute Winter Dresses - Bright Winter Dresses  

Source (clockwise from upper right): Mode-sty, Michael Kors, ASOS Curve, Boden

When the sky is gray, break out the brights to create your own sunshine. Whether you go head to toe in one color or add a punch with color blocking, choose a color you love to boost your mood.

Bold Stripes

Cute Winter Dresses - Bold Stripes  

Source (clockwise from upper right): Gap, ASOS Curve, Michael Kors, Top Shop

Cute winter dresses don’t always have to be bright colors! High contrast stripes are a great way to shake up your look. Think black and white, maybe with an extra shot of one bold color. The styles above are also shift dresses, which are great choices for active lifestyles. Shifts give you room to move without looking bulky.

Midi Length

Cute Winter Dresses - Midi Length  

Source (clockwise from upper right): ASOS, Anthropologie, CiChic, Shabby Apple

The midi trend is a perfect recipe for cute winter dresses. A longer skirt length gives your legs more coverage on blustery days. I prefer a loose skirt and fitted top in the winter. This combo makes it easy to layer a sweater on top and cozy tights underneath as needed. Plus a long flowing skirt is fun whether you’re ice skating or just twirling around! Just remember to choose a style with a bit of stretch to make staying active easy.

Wondering how to stay warm on the coldest days?

When temperatures take a dip, I add thin but warm layers underneath. Modern fabrics like merino wool or Uniqlo’s HeatTec are thin enough to layer under all your cute winter dresses without adding any bulk. Layers are key!

Inspired by my choices? Check out even more of my favorite cute winter dresses on Pinterest, and tell me your favorite winter outfit in the comments.

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