Leather skirts can feel intimidating at first glance: too tough, too bold, and too reminiscent of a certain nightlife persona we’ve all aged out of. But in reality, they’re one of fall and winter’s most versatile wardrobe staples. Unlike their breezier counterparts, leather skirts actually hold warmth, making them a surprisingly practical option once temperatures drop. In recent seasons, the style has been given the full-fashion treatment: Khaite has championed the leather pencil skirt as an essential, while runways at Chloé and Bottega Veneta have showcased a variety of full-skirted styles.

The styling potential is vast, too. Leather skirts look effortless with chunky knits and loafers, sharp with ladylike jackets and suede boots, and undeniably cool when paired with more leather. Whether you gravitate toward an elegant column silhouette, a voluminous maxi, or a fluted mini, there’s a leather skirt for every mood—and endless ways to wear it right now.

Sleek and Streamlined

Leather easily lends its sheen to a sleek all black look. A turtleneck and knee-high boots are all you need.

In the Gray

Toteme’s light gray leather skirt is an unexpected take on the style. Pair it with winter whites, including a fuzzy shearling jacket and button-up for a refreshed interpretation.

Fit and Flare

A flared maxi is a feminine, fashion-forward take on leather. Balance the shape with a chunky knit sweater and loafers.

Leather on Leather

Take a styling cue from Khaite and double up on leather. A tough jacket and a sleek maxi make for an extra cool attitude.

Penciled In

Zara’s muddy red pencil skirt might make a surprising holiday staple. It looks especially chic when paired with shades of brown.

Extra Texture

A calf hair leather wrap skirt, like this one from Lou Lou de Saison, is a luxe way to add unexpected materiality to your everyday.

Everyday Maximalism

A leather mini and a leopard topper are a match made in fashion heaven. Studded flats add a hint of off-kilter cool.