Pants Fatigue? 7 Non-Intimidating Leather Skirt Outfits to Try This Winter

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Photos: Phil Oh

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.

Vogue s Must-Have Leather Skirts

The Sleek Midi
La Ligne Vega midi skirt
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The Flared Favorite
The Frankie Shop Savil midi skirt
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The Classic Mini
Theory darted leather miniskirt
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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.

Gap

featherweight turtleneck

La Ligne

Vega midi skirt

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Staud

Wally knee high boots

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Lié Studio

The Simone earrings

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.

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Coach

shearling cardigan jacket

Alex Mill

Jo shirt

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Toteme

panelled leather skirt

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Aeyde

Tillie pumps

Fit and Flare

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

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Róhe

oversized ribbed wool sweater

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The Frankie Shop

Savil midi skirt

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Anderson s

skinny leather belt

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Gianvito Rossi

Georgie 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.

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Khaite

Hewit jacket

Khaite

Loxley skirt

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Manolo Blahnik

BB 10 flats

Celine

Triomphe 52mm sunglasses

Penciled In

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

Everlane

The Boxy turtleneck

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Zara

leather straight skirt

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Ben Bridge

Toscano bracelet

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Coach

Brooklyn shoulder bag 28

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.

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Giuliva Heritage

Lara blazer

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Cos

corduroy shirt

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Loulou de Saison

Myra midi skirt

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Rag Bone

Joni knee high boots

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.

Madewell

single-breasted topcoat

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Nili Lotan

March cardigan

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Theory

darted leather miniskirt

Bally

Beliska ballet flats

Shop More Leather Skirts:
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Madewell

x Alexa Chung Vivienne wrap skirt

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Massimo Dutti

straight leather midi skirt

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Nour Hammour

Elisse midi skirt

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Róhe

paneled snake-effect midi skirt

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Ulla Johnson

Aninda midi skirt

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Proenza Schouler White Label

Cece skirt

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The Row

Hedora skirt

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Veronica Beard

Holmes pencil skirt

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Mango

Paris midi skirt

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Chloé

inverted pleat skirt

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J.Crew

Fairfax skirt

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A.L.C.

Marta leather skirt