10 Stylish Winter Skirts to Give Your Overworked Jeans a Break (Plus How to Wear Them)

Skirts…in winter? Groundbreaking. But seriously, it can be when you’re heading out in single-digit weather. What if we told you there’s a way to slip on your slinky skirt and stay toasty this winter? Well, there is. Whether it be by layering up with thick tights, choosing heavy-duty fabrics like wool or knits that will keep in body heat or sliding on your tall boots that’ll protect your bare legs from feeling the breeze, there are many ways to make your skirt warmer. Below, we explain eight ways to style your winter skirts this season.

1. Refresh your leather skirt.

You know the drill: When winter rolls in, out comes our leather pants (i.e., our vegan Abercrombie & Fitch pair). Well, it’s time for a new leather good to grace your seasonal rotation: the leather skirt. This year, we’re embracing unconventional leather skirts with bold cuts and fabric manipulations—like hand-stitch details, embossed metal work, or an A-line pleat like the one pictured above—which will do your styling for you.

2. Throw on a matching knit set.

Whether it’s ease, comfort or looks that draw you towards matching sets, they’re always a good choice. While we love the classy look of a neutral set, we suggest opting for one with a printed pattern that will take you from office chic to streetwear sleek. Plus, the thick, heavy knit material helps lock in warm temperatures by trapping your body heat (a bonus for those in states with bitter winter weather).

3. Pair tights with sequin-adorned mini skirts.

According to our fashion editor, shopping platforms were quick to notice a shift towards the mini skirt early this year, and we don’t see that stopping anytime soon thanks to the recent sequins overhaul dominating our Pinterest feeds. From Dua Lipa to Alessandra Ambrosio, A-listers have embraced this head-turning trend, showcasing how easily it can be dressed up or down.

4. Don’t be afraid to mix formal and casual materials together.

This is the ultimate Carrie Bradshaw bodega run outfit—we’re talking about throwing your most lived-in sweatshirt over a statement skirt, like a luxurious crushed velvet, for a playful juxtaposition between two opposing attires. Slip on slingbacks that match your skirt and a statement clutch to finish off the look. (Black coffee to go, please.)

5. Combine corporate and sheer.

According to Prada’s ready-to-wear fall 2022 and spring 2023 runways, there’s no hiding from this barely-there trend. And while we were hesitant to adopt the head-to-toe sheer look in the past, we adore how a peek-a-boo mesh and lace detail at the bottom of a winter skirt looks both fashionable and sexy, without teetering on raunchy or scandalous.

6. Experiment with preppy pleats.

It can be challenging to transition your schoolgirl-inspired skirt to a winter look. Here’s the trick: Lengthier pleats offer a more sophisticated option that won’t be mistaken as juvenile. And if you’re feeling daring, pair a horizontal striped shirt with the vertical maxi to break up your figure. In fact, vertical lines create an illusion of elongation in height, naturally drawing the eye upwards while the horizontal lines break up that flow and pull the gaze inwards.

7. Opt for a denim midi skirt.

This totally vintage skirt is making a comeback, and don’t just take our word for it—major fashion mavens like Vogue, Fashionista and Who What Wear have noticed the rise of this denim gem. So, the next time you want to showcase your capsule closet, grab a denim midi in place of your baggy straight jeans and throw on a pair of high-knee boots. Cool, casual and oh-so chic.

8. Create dramatic movement with silk.

If you’re itching for an editorial outfit worthy of the front cover, then break out your trusty silk skirt and let the fabric billow in the wind. Pair this luxurious material with a long sleeve knit and oversized puffer for a spontaneous look or break out your heels and don a frilly top with fitted wool coat for a polished outfit.