The Chicest Pencil Skirt Outfits for Winter

What's the first thing you think of when you hear "pencil skirt"? The fitted silhouette is typically associated with classic workwear attire that's sometimes stuffy and uncomfortable, but over the past few seasons, fashion girls have been reinventing the style—majorly. They've found fresh, cool ways to wear it, turning this office staple into a street style must-have, regardless of the weather outside. It's just as much a summer piece as it is a winter essential.

As proof of the latter, we've highlighted a handful of the best pencil skirt outfits for winter, as spotted on some of our favorite girls in the know. Not quite sure how to work the piece into your everyday wardrobe this season? Don't worry—it's surprisingly easy to wear, and the styling options are extremely wide-ranging. Read on to see how fashion girls are working the pencil skirt into their winter looks; then shop our edit trend-forward skirts to buy now.


Style du Monde

Style a pencil skirt with black tights this winter.

A white pencil skirt is a must-have.

Pick a matching skirt set for a cool winter look.


Style du Monde

A leather pencil skirt feels so edgy.

Wear florals this winter to brighten your mood.

A checked wool pencil skirt is perfect for fall and winter.

A sweater and pencil skirt make a great work look.


Style du Monde

Stick with classic whites on top and colorful brights on the bottom.

Try styling a pencil skirt with a hoodie.

Go for a monochrome look this winter.

Shop pencil skirts for winter:

Two of our favorite things—plaid and tweed.

An eye-catching skirt you can wear to your next holiday party.

Don't yet own a velvet skirt? Then now's the time.

Next up, take a peek at all our favorite jean skirt outfits to wear this winter.