Sorry, Pants—This Winter, Wearing Skirts Like This, This, and This Will Earn You the Most Compliments
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Every winter, I find myself relying heavily on trousers and jeans to get by. My outfits are primarily pant-focused, which, when you live in a place like New York City that has long winters, tends to get old—fast. To combat pants fatigue in 2025, I’ve been researching winter skirt outfit ideas to copy anytime I feel like switching things up. The results of my findings? A slew of ensembles that won’t just solve this occasional dressing problem but might even kick my pants habit altogether. They’re that good.
For winter 2025, all types of leather skirts are dominating chic people’s outfits. Think pony-hair column skirts, ostrich-print pencil skirts, and lots of suede in rich colors like burgundy and tobacco. With them, the most popular top half is a leather bomber jacket. That or a simple shrunken sweater like the one Hailey Bieber’s been known to style alongside a leather pencil skirt and knee-high stiletto boots this season.
Speaking of boots, they’re probably the most-spotted shoe style when it comes to styling skirts this winter, with knee-high versions winning out over ankle heights. When people aren’t wearing boots, though, heels are the obvious choice. Flats are great to wear with trousers or jeans, but skirts, especially those of the midi or knee-high variety, call for a lift, even if it’s just a kitten heel. When in doubt, add a pair of sheer tights for added warmth (and style—especially if you opt for a brown pair instead of black).
Without further ado, scroll down to find 17 winter skirt outfits that are guaranteed to earn you compliments in 2025 (and cure any pant fatigue you’re already feeling this season).
Winter Skirt Outfit Ideas 2025
1. Leather Bomber Jacket + Leather Pencil Skirt + Gray Pumps
Styling tip: Match your skirt with your top and then use your shoes to add a pop of color (even if it’s just gray, as seen here on Alexa Chung).
ZARA 100% Leather Straight Skirt Limited Edition
2. Shrunken Sweater + Leather Pencil Skirt + Knee-High Stiletto Boots
Styling tip: Find a skirt and boot pairing that almost touches, but doesn’t. That little bit of exposed skin adds a sexy touch to your skirt outfit, without leaving you at risk of catching a cold in the winter.
St. Agni Brushed Leather Column Skirt
3. Turtleneck + V-Neck Sweater + Lace-Trim Skirt + Pencil Skirt
Styling tip: Don’t be afraid to layer two skirts on top of each other to make the simpler one feel more interesting.
Reformation Carolina Silk Skirt
4. Blazer + Statement Belt + Satin Skirt
Styling tip: Belts aren’t just for pants. Use one over your skirt or jacket to make skirt outfits look elegant, not boring.
SRG Sandra Silk Skirt
5. Button-Down Shirt + Fur Collar + Gray Skirt + Tights + Kitten Heels
Styling tip: If you want to wear a knee-length skirt, add tights or tall boots to make the cut feel less awkward and “leggy” in the winter.
h&m Pencil Skirt
6. Black Sweater + Velvet Column Skirt
Styling tip: During the holiday season, go wild in the skirt department, playing with textures like velvet and bold colors, like hot pink, red, purple, or yellow.
COLLEEN ALLEN Cotton Velvet Maxi Skirt
7. Suede Skirt Suit + Leather Gloves + Kitten Heels
Styling tip: Nothing will make you feel more elegant or luxe than a suede skirt in the winter. Pair yours with a matching blazer for an even more upscale outfit.
Centre Piece Jett Calf Hair Skirt
8. Leopard-Print Jacket + Pencil Skirt + Tights + Kitten Heels
Styling tip: Add some leopard print to make a black skirt feel more festive.
H&M Pencil Skirt
9. Leather Bomber Jacket + Pony-Hair Skirt + Boots
Styling tip: Don’t worry about mixing materials like leather and pony hair. No, it’s not too much. It’s just enough.
Ludovic De Saint Sernin X Zara Short Leather Skirt With Fur
10. Suede Bomber Jacket + Maxi Skirt
Styling tip: When it’s extra chilly out, cover up by pairing a maxi skirt with a bomber jacket.
COS Sheer Maxi Skirt
11. Sculpted Top + Column Skirt + Boots + Clutch
Styling tip: All-black skirt outfits aren’t boring if they have good proportions. Pair your black column skirt with a sculptural top to add interest.
Ancora Ravena Skirt
12. Fur Jacket + Leather Blazer + Leather Pencil Skirt + Boots
Styling tip: My favorite pencil skirt tip is to find one that has a slit in the front and back, like this Tom Ford–era Gucci version. It allows you freedom of movement and also looks way too chic.
Gucci Crêpe Slit Detailed Skirt
13. Leather Bomber Jacket + Maxi Column Skirt
Styling tip: If you’re craving the warmth of pants without having to wear actual pants, try a wool maxi skirt and add fleece-lined tights and boots underneath.
Reformation Layla Skirt Es
14. Button-Down Shirt + V-Neck Sweater + Plaid Skirt
Styling tip: When wearing a plaid skirt, lean into the prep of it all by adding a button-down shirt and a layered sweater with it.
MANGO Wool-Blend Check Midi-Skirt
15. Double-Breasted Blazer + Leather Skirt
Styling tip: There’s nothing easier than styling a blazer and a skirt, both in black. Lean into the simplicity of this chic outfit next time you’re stumped about what to wear.
express Editor Studio Stretch Twill High Waisted Maxi Skirt
16. Blazer + Two-Tone Skirt + Round-Toe Pumps
Styling tip: Break up an all-black skirt outfit with a touch of white. It doesn’t have to be a lot, but it’ll make a big difference.
LIONESS Anchored Midi Skirt
17. Fur-Trim Jacket + Lace Top + Animal-Print Pencil Skirt
Styling tip: For a night out, pair some sort of animal-print skirt with a lace top for a fun, unexpected outfit that your friends will wish they thought of first.
Róhe Ostrich Satin Column Skirt
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