I’m Dress Obsessed—Here Are 27 On My Winter Wish List

I will not disclose the number of dresses currently hanging in my closet right now (insert embarrassed face emoji here) but let’s just say I have a slight obsession when it comes to the easy-to-wear staple. And just because it’s winter, it doesn’t mean I’ll be casting them aside anytime soon. In fact, I love a good winter dress-tights-boots situation and there are certainly plenty of fresh new frocks currently piling high on my winter wish list right now.

Since we’re skipping the office holiday parties and big festive soirée’s this year, today I wanted to highlight some of the more casual winter dresses to slip into this cold-weather season. These strike the perfect balance of cozy and chic—some ideal for lounging, others perfect for a casual winter walk, or a holiday dinner with the family. Take a peek below and pair these casual winter dresses with your favorite slippers, boots, and cozy layers this season.

I have my eye on this one for Thanksgiving.

This also comes in ivory but I love the sky blue hue of this unique bolero dress.

Just add black tights and chunky boots.

Style with chic black knee-high boots and a chunky cardi.

This looks seriously luxe (and comfy!).



This dress has two of my favorite things—a retro collar and ribbed knit fabric.

Guaranteed this will be your winter go-to.

Style with similar cream and ivory hues for a sumptuous winter look.

I'll be wearing this over a tissue-thin black turtleneck this holiday.



A collared dress that strikes the perfect balance of cozy and chic.

The iconic Hillhouse nap dress gets a welcome winter update.

I'm 100% here for a billowy silhouette.

The perfect lounge dress, found.



For a cozy winter look add suede knee-high boots and a soft shearling coat.

We love a turtleneck mini dress.

Perfect for layering over turtlenecks and tights.

Elevate your look and style this warm knit dress with a chain belt.