Anyone who knows me will know that I'm almost always in skirts or dresses, so even though it is February, I gladly take on the challenge of integrating skirts into my cold-weather wardrobe. And this season I've been enamoured by the span of strong offerings. You likely note the recurring trends — from leather skirts (an annual resurgence synonymous with cooler weather) to voluminous and knitted skirts, in addition to the fresh trends of 2025, namely tailored pieces and parachute skirts. When it comes to styling skirts for winter, the options are aplenty, although I'm aware knowing where to start when approaching skirt styling from a cold weather standpoint may feel daunting as they're best associated with spring and summer.
I tend to adjust proportions depending on what style of skirt I'm wearing. As you'd expect with the season, extended hemlines tend to feel most weather-appropriate but while the weather behaves I can get away with wearing them bare-legged paired with outerwear to ensure warmth and comfort. I like the option of pairing elevated basics with form-fitting suede skirts and cinched-in blazers with full voluminous skirts and while we're thinking outside of the box, why not pair your skirts with jackets in a matching hue, for a uniform look? All things considered, it's evident I don't have to sacrifice one of the most loved pieces in my arsenal this season and there are a myriad of opportunities to integrate summer styles into your winter wardrobe. Continue reading for five elegant skirt outfits I intend to wear from here on out.
5 Elegant Skirt Outfits I'll Be Wearing This Winter:
1. Suede Midi Skirt + Black Lightweight Top + Mary-Jane Shoes
Style Notes: Note Nnennae's expert styling as she juxtaposes leather and suede textiles in this tonal outfit. She also shows how to style the mesh Mary-jane flats this season.
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One of the most directional leather coats I've witnessed, thus far this season.
A long sleeved T-shirt is a piece you can easily dress up, or down.
Opt for a warm caramel brown instead of the black leather midi skirt.
Mint Velvet's mesh pumps look every bit as good as the designer offerings.
2. Blazer + Full Skirt + Mary Jane Platforms
Style Notes: Our very own Maxine Eggenberger is a prime example of refined elegance and she donned this classic ensemble to London Fashion Week. The outfit comprised fitted elements to free-flowing skirting, with sleeved coverage that works well for the change of seasons.
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The favourite of many Fashion Editors.
The taught waistband transforms this white midi skirt into a formal piece.
Sezane always comes through with the French staples.
I have it on good authority that this handbag is worth every penny.
3. Red Jumper + Leather Skirt + White Pumps
Style Notes: Pairing this season's coveted hues together is a fresh take on winter styling. Red and burgundy is an expert colour combination.
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A soft and cosy knit, in a gorgeous deep red from one of our favourite brands.
You can always rely on Whistles for premium leather goods that'll stand the test of time.
Tod's has been everywhere this season and this bag is just calling my name.
The pleated satin detail is my favourite.
4. Knitted Skirt + Turtleneck Top + Pumps
Style Notes: Like Abi, opt for textured fabrications like a woollen skirt, paired with a seam-free top for a bodycon finish.
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Is it even winter without a classic black turtleneck in your wardrobe rotation?
The perfect way to wear skirts this winter.
So chic!
Everyone I know seems to be reverting back to top-handle bags this year.
5. Dark Wash Denim Skirt + White Jersey Top + Knee High Boots
Style Notes: A dark-wash denim skirt with a white jersey top feels elevated even in the winter, while knee-high boots add a modern edge. Perfect for daytime outings, this look strikes the ideal balance between casual and refined.
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One word, chic.
The ultimate layering T-shirt.
This exact piece is high up on my wish list. I intend on pairing it with a crisp white shirt.
You can never get me to say anything bad about Paris Texas boots.
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