A midi skirt might not be the first thing you reach for when it comes to building a winter outfit, but Instagram's best-dressed have been making a pretty good case for the calf-skimming hemlines lately. While each person offers their own spin on the wardrobe staple, the uniting theme seems to be wearing your skirt of choice with a stylish jumper, be it a chunky roll-neck, ribbed fabric or a pop of paintbox brights. The midi-skirt-and-jumper look has become a particular favourite of fashion minimalists such as Alexis Foreman and Brittany Bathgate, who tend to stick to versatile colourways of navy, cream and black. And the result? And super-chic look that massively satisfies my smart, classic taste.
Another uniting theme is contrasting textures, and the simplest of pairings can become instantly elevated when you experiment with fabrics. I'm thinking about Alexis's leather-skirt-and-wool-jumper get-up and Monikh Dale's tulle-skirt-and-chunky-crew-neck pairing, both of which pack their own personality but feel undeniably pulled together. So if you're not sure how to wear your favourite midi skirt as the mercury drops, feel free to use the below outfits to spark your imagination. Scroll down for the seven midi-skirt and jumper outfits to try this year.
Midi-Skirt-and-Jumper Outfits to Try for 2025:
1. Leather Midi Skirt + Oversized Knit + Knee-High Boots
Style Notes: A leather skirt and oversized jumper in matching shades are an easy way to make a statement, as seen on Alexis. Plus, have you seen those amazing knee-high boots? I'm in love...
Shop the Look:
So cosy.
This A-line fit is stunning.
The right scarf can elevate any outfit.
Everyone could get a lot of wear out of this boot.
2. Tutu Midi Skirt + Chunky Crew-Neck
Style Notes: For a low-key party look, make like Monikh and throw on a chunky crew-neck knit over a frothy tulle midi skirt.
Shop the Look:
Baby blue suits so many skin tones.
Unleash your inner ballerina with this playful tulle skirt.
These look a lot more expensive than they are.
The perfect size for an evening out.
3. Argyle Jumper + Pencil Skirt
Style Notes: An argyle knit and pencil skirt combo is one that you can easily take from the office to a dinner date. Add some classic black court heels to pull together the look.
Shop the Look:
You can also tuck this into jeans for more casual days.
Great for in or out of the office.
You can't beat a classic.
4. White Roll-Neck + Navy Midi Skirt
Style Notes: I love the classic pairing of cream and navy, especially with the addition of chunky leather boots. Cool, stylish, cosy and just perfection.
Shop the Look:
This is definitely a wear-everyday jumper.
A satin skirt is a must-have.
*Adds to wish list*
What a great pair of boots.
5. Fitted Turtleneck + Silky Slip Skirt
Style Notes: Slip skirts can look really sophisticated if you pair them with a smart turtleneck and a pair of classy black boots, as Chloe proves.
Shop the Look:
I'd also style this oxblood shade with camel and beige tones.
Nobody's Child slip skirts never disappointed.
So chic.
6. Cable Knit + Black Skirt
Style Notes: I'm a big fan of neutral knits and black skirts. This casual take on the outfit combo is particularly great for weekends.
Shop the Look:
This buttery cream shade is divine.
The perfect winter skirt!
This shaping is so classic.
These loafers have proven to be a staple winter piece.
Just a little pop of colour.
7. Slouchy V-Neck + Circle Skirt
Style Notes: There's something so old-school Hollywood about circle skirts. Team yours with a slouchy jumper for a more modern look.
Shop the Look:
I love this shade.
Navy works well with just about every colour (yes, even black).
Iconic. That's the only word.
These are my dream slingbacks.
This story was originally published at an earlier date and has since been updated.
-
6 Fashion Editors, 36 Summer Buys—Inside Our Summer 2025 Mood BoardsEverything inspiring our wardrobes this season.
-
If I Saw You in Any of These 15 Summer-to-Fall Transitional Outfits, I'd Think You Hired a StylistNice taste.
-
Put Down the Black and White Pants—This Is the Richer Color You Didn't Know You NeededElegant and on-trend.
-
10 Outfits Europe's Chicest Dressers Are Wearing When They're *Not* on VacationStaying local is cool.
-
What You Should and Should Not Wear to Every Major Sporting EventFrom a Liberty game to the French Open.
-
Just to Be Clear, *These* Are the Pants Fashion People in L.A. Are Wearing Instead of Basic JeansSpotted in Paris too.
-
The Coolest Outfits of Summer 2025 Are Actually the Laziest—Let Me ExplainEasy does it.
-
When I'm Not Shopping Amazon Prime Day, It's These Chic Deals (Ahem, J.Crew, COS, and Banana Republic)On-trend finds you won't want to miss.
