Come winter, aside from the obvious seasonally appropriate staples (cue wool coats, leather boots and cashmere knits), my most-worn piece is easily a grey wool skirt. My collection includes one full-length style, with a crossover flap and decorative buttons at the hip; another in deep charcoal, box-pleated and calf-grazing; a mini version fastened with a traditional Highland kilt pin to guard against gusts; and a lighter wool-cotton blend that sees me through those early, deceptive weeks of autumn warmth. All of them are vintage, unearthed in charity shops or found during the depths of resale app doom-scrolling.
For the past few years, these grey woollen skirts have become the backbone of my cold-weather wardrobe, their blanket-like thickness relied upon when the temperatures plummet, and their quiet polish unmatched in my eyes. Perhaps it’s their nostalgic pull: like many of our most-loved garments these days, they carry echoes of the past. The memory of my secondary-school uniform, a charcoal skirt, scrawled with Tipp-Ex and rolled up at the waistband, for example, which I suppose in retrospect you could call an early exercise in personal styling.
Now, years on, my grey wool skirts occupy a place of pride in my autumn/winter wardrobe. Unlike their louder tartan or check-print cousins, which were everywhere at fashion month, the plain grey wool skirt is understated, quietly powerful, and even a little subversive. Something you might initially dismiss as “grannish” proves, when styled right, to be the epitome of pared-back chic.
“I have three grey wool skirts on a perennial loop: a Forza Collective full pleat number, my Saks Potts skirt set with a little cropped matching jacket, and a speckled centre-split ankle length skirt from MKDT,” says Isabella Rose Davey, the forever stylish COO of Copenhagen Fashion Week, who has spent the past six years in the Danish capital. “I am a creature of habit, and while my boyfriend will vouch for my expansive wardrobe as a continued point of contention in our fight for space in our little Copenhagen apartment, I tend to wear the same set of clothes regularly. A good boot, a great jumper, and a smart skirt is an equation I tend to repeat.”
For me, a similar equation applies, if you swap out a cozy knit for a crisp shirt for sharpness or a striped rugby polo for ease, and loafers or slim retro sneakers in lieu of good boots. When it comes to outerwear, well, the options are endless–be it a nylon bomber, leather jacket or coordinating wool coat–the pleated skirt goes with everything. “When I think of the wonderful uniformity of a grey wool skirt, my natural association is to pair it with something unexpected, as much complementary,” Davey adds.
On the fall/winter 2025 runways, the grey wool skirt was everywhere—from Prada’s crumpled, cropped and deconstructed versions to Vaquera’s oversized pleats and buckled belts, paired with inky silk shirts. Andreas Kronthaler for Vivienne Westwood offered a punkish twist, with one side cut raw to reveal the leg, rendered in tweed.
The spring/summer 2026 shows also confirmed the skirt’s staying power. One grey wool pencil skirt in particular, at Matthieu Blazy’s reimagined Chanel, has already jumped to the top of my dream wish list – fastened with gilded buttons at one side, worn low on the hip with a matching cropped jacket and finished with a thin belt. Meanwhile, other brilliant streamlined and full-skirted versions also appeared at Vetements, Fendi and Jil Sander.
Off the runway, the grey wool skirt has found its place in pop culture, too. Just this week on The Traitors, Claudia Winkleman wore a perfect pleated Prada iteration, styled with an oversized studded belt and slouchy knit, courtesy of stylist Sinead McKeefry.
It’s easy to see why this quietly luxurious staple continues to endure. “They look great with the clothes I already own and they make me feel sharp, put together and most importantly, proud to wear local design,” Davey concludes. Made from honest materials, wonderfully simple in design, yet unmistakably polished, if there’s one addition your winter wardrobe needs, we can confirm that it’s a grey wool skirt.
