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Skirts are among the most slept-on pieces in our winter wardrobes. (And I obviously mean slept-on in the colloquial sense—not the literal one.) We’re so caught up in our winter coats and our winter boots and our winter scarves (and hats and gloves) that winter skirts get the short end of the sartorial stick. They’re excluded from our mental pictures of our winter wardrobes, which tends to mean they’re excluded from our actual winter wardrobes, too. Because if we don’t think to buy them, we don’t buy them—and we don’t have them to enjoy all season long.
Some good news (which is also low-key bad news): Winter isn’t going anywhere any time soon. The first day of spring doesn’t officially arrive until March 20, which means we have a solid two months of frigid temperatures to endure before any shred of warmth returns to our lives. The upside of this is, of course, that it’s not too late to stock up on winter skirts. It’s, in fact, the perfect time to do so, because peak winter fashion season has passed, and tons of cold weather-friendly pieces are already seeing mark-downs.
So don’t hesitate. There’s a genuine plethora of winter skirts just waiting to meet their style soul mate. They’re here, they’re on-trend and they’re ready to help you stay warm in the chicest, most stylish way possible. So stop sleeping on them—all they want to do is make your life better.

A classic pencil skirt with a contemporary twist—rendered in an autumn-winter color palette.

This sleek skirt is downright irresistible.

A sweater. In skirt form. (You’re welcome.)

Because if you’re the kind of person who’d buy and wear a fringe skirt, there’s no reason you shouldn’t make that happen for yourself.

This year’s chicest animal print is ready to diversify your winter skirt collection.

It’s winter—the more plaid, the merrier.

Because when it’s cold out, I can’t help but stock up on every corduroy piece I see.

Nothing says winter quite like metallic gold, well, anything.

This knit skirt comes as part of a matching set—and it’s sure to delight whether or not you shop it with its sartorial buddy.

Because we could all use more leather (or faux leather) pencil skirts in our lives.

Plays well with your go-to oversized sweater—and your go-to chunky boots, too.

A classic skirt silhouette in a classic winter shade.

Not your average pleated midi skirt.

If this skirt has convinced me of anything, it’s that velvet and chevron are a match made in sartorial heaven.

Because cold weather and mini skirts are far from mutually exclusive.

Never underestimate the value of a versatile basic.

This tiered midi will take you from season to season. Just swap out your layers, and you’re set.

Is any closet complete without at least one plaid pencil skirt?

Sequins and fringe make for a seriously unstoppable (and winter-friendly) going-out combination.

A pleated leather wrap midi is the kind of thing you could’ve never dreamt up. But once it’s sitting right in front of you, you know you have to have it.

Don’t sleep on satin—one of autumn/winter’s favorite textiles.

Equal parts cozy, shiny and absolutely delightful.

It’s cute. It’s statement-making. And it’s less than $30.

Winter might be the season of the all-black-everything ensemble, but that doesn’t mean color is off the table—far from it.

Metallic. Leather. Pencil. Skirt. Need I say more?

Give me velvet anything in the winter, and I’ll be happy.

Oh yeah, winter maxi skirts are totally on the menu.

BRB, stocking up on every knitted midi I come across.

Sweater pencil skirts are a straight-up gift. (I didn’t know these existed, but now that I do, I’m hooked.)

Quite possibly the most stylish way to keep your ankles warm this season.

Throw this on with your comfiest snow shoes and your favorite vintage tee, and you’re in business.
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By providing your information, you agree to our Terms of Use and our Privacy Policy. We use vendors that may also process your information to help provide our services. This site is protected by reCAPTCHA Enterprise and the Google Privacy Policy and Terms of Service apply.