The Fail Proof Ways To Style A Dress This Winter

Each year, usually right around this time, I come to the repetitious realization that winter is nigh. Despite how quickly summer and autumn seem to come and go, the reality of frigid temperatures and inclement weather is very, very real. Of course, it’s not all bad — that’s why cute coats and chic boots were created! But there’s no denying the fact that dressing for wintry weather can feel like a chore once you’ve done it enough days in a row. And once this feeling of ‘work’ begins to be associated with your personal style, pieces like dresses and skirts are often swapped for sweats and leggings. In an effort to avoid a style rut, I proactively came up with a few outfit ideas for wearing dresses in cold weather.

Implementing a few styling tips I’ve gathered from looking at hundreds (thousands?!) of street style and Instagram looks over the years, I put together four outfits that I know I can turn to in my gloomiest hours. From a useful layering tip that works with countless separates in my wardrobe to an out-of-the-box outfit combination that reliably feels fresh, continue ahead for some quick, easy inspiration for the months ahead.

Cottagecore Continuation

I know everyone has probably had their fill of the Cottagecore trend by now, but this whimsical take on dressing translates well to wintertime, especially if a full-skirted plaid dress is involved. I layered a quilted green jacket on top of my TOAST dress and accessorized with an oversized cashmere scarf to keep it cozy. Below, socks and clogs cemented the vibe. If it’s really cold out, I’ll switch to a heavier parka and add tights beneath my socks for added protection.

Dress-Over-Pants

One of my all-time favorite styling tricks is layering a dress over pants. While the proportions can sometimes be tricky to get just right, I’ve found that a mini hemline worn with a crop-flare pant silhouette is reliably strong. And I know, I know — you can wear color in the winter. But sometimes an all-black outfit feels just right, as illustrated above.

Turtleneck to the Rescue

Once cold weather comes around, the single most important layering item in my closet is a turtleneck. Not only does it keep my neck toasty, but it also makes it possible to wear pieces that might otherwise not work for chilly temperatures, like this leather tunic dress from Rebecca Taylor. And because the hemline is short, I wore tights with tall boots to split the difference.

Chunky Footwear Trend

I’ve always struggled with styling sweater dresses — while in principle I think they’re great pieces for winter, it can be difficult to find the right footwear combination. Recently, I tried throwing on a pair of chunky shoes to see how it looked and the outcome was a little ‘90s- inspired and well-balanced. On top, I wore a cream-colored leather jacket in lieu of my normal black coat for more of a statement look. If it’s super cold, I’ll add an oversized black coat on top of everything.