The 90s were a defining decade for many reasons: technology was simpler, pop culture peaked, and of course, the fashion was so iconic that its influence still shows no signs of slowing down. From sharp tailoring and power dressing to slip dresses and capri pants, the era’s most recognisable trends are back on the trend map for 2026.
In the latest episode of HELLO!'s Style Surgery, host and style expert Karen Williams is joined by stylist and broadcaster Laura Puddy and Lauren Ramsay, H! Fashion's Deputy Digital Editor, to discuss the 90s icons and style staples that continue to influence our wardrobes.
"To be honest with you, I feel like most of my wardrobe now is kind of what I was wearing in the 90s, just a bit more polished," Karen explains. But there's one particular nostalgic favourite that deserves a closer look for autumn/winter 2026: stirrup leggings.
When Laura brings up the once-ubiquitous style, Karen is immediately on board. "I'm here for them, with a little kitten heel," she says.
© GC Images
© GC ImagesWith their distinctive foot loop, stirrup leggings offer a stylish alternative to classic black leggings, bringing a subtle retro feel to everyday outfits. Practical, versatile and surprisingly easy to style, they work just as well with an oversized knit as they do with a tailored blazer and a pair of elegant heels.
Their latest resurgence makes sense, as 90s-inspired dressing continues to influence the way we shop in 2026. Stirrup leggings offer an easy way to tap into the era's understated aesthetic - a pared-back basic that does all the talking with the tiniest detail.
How to style stirrup leggings for autumn/winter 2026
The strap beneath the foot works perfectly with all kinds of footwear, from ballet flats and loafers to pointed-toe boots and kitten heels.
The key to wearing them now is to balance their slim, simple silhouette with fun layers. For daytime, black stirrup leggings with loafers, a crisp white shirt, and a long coat is an easy way to look refined. Ballet flats are another perfect partner, particularly for anyone who wants to lean into the balletcore aesthetic.
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© Getty ImagesColour is worth considering, too. Classic black will always be the easiest option to wear, but chocolate brown, charcoal, burgundy and other muted neutrals will bring interest to any look.
Stirrup leggings have retained their appeal by being practical, flattering, versatile and affordable. And with the current appetite for nostalgic dressing showing no sign of fading, they could be one of the most useful additions to your autumn/winter 2026 wardrobe.
Shop our favourite stirrup leggings for AW26:
Black Ponte Stirrup Leggings
Next
These Next leggings are a classic, comfortable design at an incredible price point. They also come in regular, long and extra-long lengths.
Brown Ribbed Jersey Stirrup Legging
Nobody's Child
Chocolate brown is the perfect alternative to black for a look that feels a little more luxurious, yet still completely versatile.
Caserta High-Rise Stirrup Leggings
The Frankie Shop
We love the piping along the front of these The Frankie Shop leggings for an added preppy touch.
Rosa Lace Stirrup Tights
Swedish Stockings x Free People
Lace stirrup leggings are my favourite for an evening outfit. Simply pair them with some black pointed stilettos and a waist-cinching black blazer.
River Dual Airweight Stirrup Legging
Splits59
Burgundy is a major trend this season. Pair these with a fluffy jumper and your comfiest shoes for a cosy daytime ensemble.
High Waisted Stirrup Leggings
Zebra-Print Leggings
For those who love a statement look, these Roberto Cavalli babies are a must-have.
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