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This winter, forget denim as your go-to layer; we’ve officially entered the season of the skirt. Once December arrives, longer styles are immediate musts when looking for chic ways to dress for the outdoors. However, you can enjoy the wintertime look when you’re battling any level of chill. Just ask fashion people in Los Angeles and Paris; despite their opposite aesthetics and geography, they’ve found a common thread in the power of pairing reliably sharp skirts and boots together, specifically the combination of a knee-length skirt with knee-high boots.
The most popular method for wearing skirts and boots on both coasts is combining complementary styles that provide full coverage from head to toe. It doesn’t matter if your skirt features allover prints, edgy distressing, or a sleek slit; a knee-high boot instantly adds a sturdy polish that smoothly completes any outfit—and it appears low-heeled versions.
Knee-length and midi skirts themselves exude a distinct elegance that can sharpen up any winter look. The piece is more dressed-up than jeans, but less formal than a full-length dress. Plus, their longer silhouettes and varying fabrications allow for endless color-blocking play—especially when you add a versatile boot that can effortlessly transition from day to night.
There are plenty of accessories that can further elevate the winning combination. Fashionable inhabitants of both cities are gravitating to every variety of top layers, from fluffy coats to monochrome knits. Pairing those with reliable sunglasses and a shoulder bag is a surefire way to keep your wardrobe warm and perennially chic—which you can discover in full, below.
Slit skirts are a perfect complement to knee-high boots. The two different heights create full leg coverage, which practically keeps you warm while creating a streamlined, stylish appearance. A trending shaggy coat makes the perfect cozy, yet glamorous top layer with a burst of whimsical texture.
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We predict soft and cozy days ahead.
Citizens of Humanity
Varra Rib Henley
Endless Rose
Front Slit Maxi Skirt
Perfect for day-to-night dressing.
Matching sets are the blueprint for a look that’s instantly put-together—so don’t discount the skirt suit when dressing this season. A blazer-and-skirt set creates a polished effect that you can layer over just about any top options. Plus, neutral boots—like this two-toned brown style worn by Destiny Joseph—provide a clean base for tonal shades like greens, blues, and purples to stand out and make a colorful statement. Allover textures like tweed will also provide additional dimension that’s intriguing and eye-catching.
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ASTR the Label
Bellmere Jacket
Ulla Johnson
Andi Knit Tweed High Waist Skirt
Jeffrey Campbell
Sincerely Boots
We’re crushing on chocolate brown right now.
Gucci
Horsebit 1955 Leather Shoulder Bag
A versatile shoulder bag transcends seasons.
Monochrome dressing is always a reliable go-to for any outfit—and knee-length skirts and boots are no exception. Take content creator Kelsey’s look, which utilizes black tones across a leather trucker jacket, smooth skirt, and low-heeled boots. Her footwear’s subtly squared toes add a geometric touch, while a woven handbag brings the outfit a burst of texture.
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Marks & Spencer
Faux Leather Lightweight Jacket
This skirt can be easily dressed up or down.
8 Other Reasons
Emily Shoulder Bag
Woven textures aren’t just for spring.
Low heels are chic and modern.
Don’t be afraid to divide your skirt and boots with some high contrast. If your footwear veers the darker route—like this deep brown leather pair—make a statement with a lighter-toned outfit. A white turtleneck and complementary skirt create a stylish monochrome set, with additional dimension from a skinny buckled belt.
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FLORE FLORE
Dinah Turtleneck Top
An effortless winter turtleneck
French Connection
Harry Suiting Slit Maxi Skirt
This silhouette works for any season.
Sam Edelman
Porter Knee High Boot
Subtle squared toes add geometric flair.
Favorite Daughter
The Lady Leather Belt
The logo-less hardware is so sleek.
“Sandwich dressing” reigned supreme in 2025, and it’s a no-brainer when choosing a skirt to pair with your boots this winter. Like the outfit above, match your top with your boots, then mix in a skirt in any hue or texture. Similar shades will look truly effortless, like this creator’s look—which placed a deep chocolate brown skirt between an equally dark black turtleneck and stiletto-heeled boots. Oversize sunglasses and a soft leather bag complete the trio with a polished touch.
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J.Crew
Feather Jersey Turtleneck
A simple knit is our cold-weather hero piece.
Massimo Dutti
Flowing Flared Skirt
Dark brown is a perfect winter neutral.
These boots were made for walking.
Prada
Prada Eyewear Collection Sunglasses
Oversize shades are dramatic and protective.
Talk about a triple threat! Like most outfits, skirts and boots can be easily paired together in a palette of mixed neutrals. A classic black leather knee-high boots, for example, makes a sharp base for other pieces in the basics family. This look pairs the style with a white skirt and tan coat, before being complemented by a matching black bag.
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Toteme
Signature Wool Cashmere Coat
COS
Merino Wool Crew-Neck Sweater
Jil Sander
Shiny Double-Face Textured Midi-Skirt
Contrast white and black shades for a two-toned effect.
Free People
Date Night Tall Boots
Narrowed toes are trending.
