5 Chic Winter Outfits Featuring Pretty Skirts

last updated 15 December 2022

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This conversation started in one of my group chats, where the most pressing fashion advice is gathered. Among our conversations is addressing the question "How do you wear a skirt in the wintertime?" The usual default for cold weather is your trusty trousers or warmest jeans, but sometimes it's nice to dress up regardless of the weather. So if you're looking for a chance to pull out your favorite skirt or new ideas for styling it in the winter, then you've come to the right place.

For updated inspiration, I've turned to the internet fashion set for how they are styling their best skirts for winter. These looks also involve classic winter staples and chic new pieces from luxurious cashmere sweaters to everyday T-shirts to functional boots. And, for warmth, the layering necessities including quality tights, mid-weight jackets, and longline coats.

All of this and more are below, where I've shopped out five flirty new skirt looks for your dressing-up pleasure. And, of course, for you to share in the group chat.

Sweater + Circle Skirt + Kitten Heels

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Theory

V-Neck Sweater in Feather Cashmere

Bel Kazan

Elora Skirt

Bruno Magli

Matilde Slingback Pointed Toe Pump

Vavvoune

Efa Leather Bag

Sweater + Miniskirt + Tights

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Reformation

Elvezia Regenerative Wool Turtleneck Sweater

Superdown

Becky Ruffle Tier Skirt

Wolford

Velvet De Luxe Semi-Opaque Tights

Bar III

Paz Lug Sole Loafers

Cardigan + T-Shirt + Denim Midi Skirt

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Everlane

The Cashmere Cardigan

Time and Tru

Short Sleeve Crewneck Tee, 2-Pack

Urban Renewal

Remade Overdyed Denim Maxi Skirt

Dolce Vita

Nestly Bootie

Leather Blazer + T-Shirt + Quilted Skirt

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Bb Dakota by Steve Madden

Rock Star Faux Leather Boyfriend Blazer

Mango

High Collar Ribbed Knit Sweater

Tory Burch

Quilted Blanket Wrap Skirt

Sperry x Who What Wear

Duck Float Zip Boot

Longline Coat + Bodysuit + Pleated Skirt

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Noize

Alizeh Faux Leather Trench Coat

Intimately

Under It All Bodysuit

J. Crew

Pleated Pull-On Midi Skirt

Schutz

Mikki Up Block Leather Boot

Next: This Once "Ugly" Skirt Trend Is Extremely Cool Now

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Copelyn is a freelance fashion and accessory editor. She formerly worked for Who What Wear as an associate shopping editor and is based in New York City. She writes about fashion and accessory trends in addition to creating original content. Before her time at Who What Wear, Copelyn was at Bustle Digital Group, working on the accessory market for cover shoots and fashion features across Nylon, The Zoe Report, Bustle, Romper, and Elite Daily. Copelyn also previously worked at InStyle and Cosmopolitan in the fashion and accessory departments on shopping and fashion market. Copelyn has a journalism degree from the University of North Carolina at Chapel Hill. In her spare time, Copelyn freelances in graphic and web design in the fashion-and-lifestyle space. She also loves to upcycle clothing and home décor as well as collect an embarrassing number of colorful sneakers and experiment with her hair color.