6 Strong Winter Outfits Featuring Chic Skirts

Joggers, knit pants, and stretchy jeans may be go-to's at the moment, but if you are looking to feel your best getting a little bit more dressed up can make all of the difference. In search of a chic outfit idea to wear with a skirt this fall and winter? Well, you've landed in the right spot. That's right—we scrolled through the feeds of some of our favorite fashion follows to uncover simple yet chic looks that could be worn with those pretty skirts that may not be getting as much time out of the closet as they were this summer. Although the temperatures have begun to drop, these flirty pieces still deserve to have a moment in the limelight.

Here, we're talking about ensembles that feature cozy knits with those trusty skirts, looks teamed with knee-high boots to add extra warmth, and so on. With all that in mind, keep scrolling to uncover the strongest winter outfit ideas with skirts. You'll also find the hottest skirts on the market right now combined with a smattering of inspired shopping picks in case you're interested in adding an unexpected fresh piece or two into your winter wardrobe. These six ways to wear a skirt during winter are foolproof.

Chic outfits featuring winter skirts



A flowy skirt with a simple sweater and flat boots is modern yet classic.

Shop the look:

The buttons make this knit like a luxe find.

Call me an outfit repeater, but I'd have this skirt on replay.

If you're looking for a new everyday bag, here she is.

Tuck a turtleneck into a black skirt for an elevated vibe.

The little updates to your classic gold hoops make the biggest differences.

The way I pounce on anything suede this time of year.

How to wear a skirt in winter



A coordinating set and a leather jacket is quite chic.

Shop the look:

The belt is removable, so it's kinda like two jackets in one.

Ok but imagine how this skirt would look with a knee-high boot.

Stilettos are 10 times more comfortable when they come in boot form.

Chic outfits with skirts



Try a trendy gilet with a longer black skirt for a very current vibe.

Shop the look:

I've been eyeing this vest all season, and it would look so good with a great skirt.

This bag looks way more expensive than it is.

Block-heeled loafers are the way to go.

Play with textures with a leather-shirt-and–silk-skirt pairing.

This fool-proof shirt looks good on everyone.

Sweaters like this are my WFH essential.

A plaid shacket is no-fail with a midi skirt and loafers.

Shop the look:

The subtle green tones are begging for my attention.

I can guarantee you'll get plenty of wears out of this.

I love topping off my knits with more knits.

Up Next: I Found the Perfect Holiday Outfits For Us—You're Welcome

This story was originally published at an earlier date and has since been updated.