“Leggings have been derided and adored, belittled and exalted over the years,” wrote Vogue’s shopping editor Joy Montgomery in her quest to make leggings “cool” again in 2026. Her case was a convincing one, styling the skin-tight style with everything from a utility-style khaki cropped trench coat to a tailored blazer and an oversized vintage Fair Isle knit. “Even as a 30-something who still experiences mild PTSD from the pairs I wore under dresses and skirts in the mid-Aughts, I’ve found myself looking at leggings with fresh eyes: as potential weekend and office wear,” she wrote.
Indeed, the gym class staple has found a purpose far beyond exercise, witnessing a full-blown reimagining. Now a regular fixture on the runways and among the street-style set, leggings have become a feature of more considered styling. And the black legging, in particular, is perhaps the most failsafe place to start.
Joining the ranks of other hardworking basics, like a white T-shirt or tank, a good pair of black leggings can do considerably more than their reputation might suggest. A blazer, cashmere knit and a pair of polished leather loafers can take leggings well beyond the treadmill, while a longline coat and a chunky scarf make a convincing case for them as a cold-weather staple.
And thanks to a roster of brands such as Toteme, The Frankie Shop, and Leset, all of which have rewritten the blueprint for leggings with considered cuts and directional details, finding a pair that feels genuinely chic has never been easier.
As we ease into the colder months of the year, here’s to making the most out of our staple pieces – beginning and ending with these eight black legging outfits.
The autumnal outfit
Reiss
Suede Funnel-Neck Bomber Jacket
H&M
Shirt
H & M
Flared Sports Leggings
WHISTLES
Black Mary Jane Ballet Pump
UGG
Enwrap Clog
Gucci
Mega Web Trademark Medium Duffle Bag
Shop more of the best black leggings:
Alo Yoga
High-Waist Airbrush Leggings
Marks & Spencer
High-Waisted Stirrup Leggings
Gap
X Victoria Beckham Mid-Rise Split-Hem Ponte Trousers
COS
