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Trends come and go, as we all know, but not all of them make a welcome reappearance when their time finally rolls back around.
Wedges, particularly the chunky styles that reached peak popularity in the 90s and early 2000s, have long been considered one of fashion’s most divisive shoe trends. Some people love them for their practicality and nostalgic appeal, while others deem them too chunky to be elegant and still associate them with some of the more questionable Y2K-era looks. But whether you’re a fan or not, one thing is undeniable: wedges are officially back!
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90s Wedges Are Back
A-listers and fashionistas, including Jennifer Aniston, Britney Spears, Mariah Carey and more were obsessed with wedges throughout the 90s abd early 2000s, often styling them with bootcut jeans – another major trend currently making a comeback – as well as slip dresses, capri pants, mini skirts, and cropped trousers. It wasn't hard to see the appeal, as they offered extra height without the discomfort of a stiletto heel, making them a favorite for everything from red carpets to casual street style and everything else in between.
Espadrille wedges in particular became synonymous with effortless spring/summer dressing in the late 90s and early 2000s, thanks to celebrities and supermodels alike regularly wearing them off-duty. Meanwhile, chunkier platform wedges leaned into the decade's love of bold, statement-making fashion, which 2026 is slowly paying homage to.
Check out some of the trendiest celebrities wearing wedges now and even a few years ago, proving they were ahead of the curve before the trend's full-blown revival!
Kate Middleton And Jennifer Aniston
Wedges even have the royal seal of approval, so what more do we need? The Princess of Wales has worn wedge espadrilles for years during more casual royal engagements (as has Meghan Markle, for what it's worth) often pairing them with breezy midi dresses and tailored summer pieces alike. One of the most memorable moments came when she wore them alongside a summer dress in Mumbai, India, and even managed to play soccer in them for a charity event… just wow!
The Friends alum loved wedges back in the 90s, regularly wearing them during her Rachel Green era alongside slip skirts, tank tops, wide-leg pants, and other quintessential 90s staples. She has continued wearing them in recent years too, pairing a stylish pair of wedges with a chic floral summer dress while filming Murder Mystery and proving the footwear trend still works decades later.
Naomi Watts And Katie Holmes
The All's Fair actress proved that wedges work just as well with glamorous dresses as they do with more casual daytime outfits when she paired hers with a white broderie Anglaise maxi dress for a Saks x Amazon party last summer. The elevated shoe added height and elegance while still maintaining the effortless feel that wedges are known for.
The Dawson's Creek alum, meanwhile, styled hers in a far more relaxed and understated way by pairing them with black trousers and a light-colored sweater in New York City last year. Katie has become known for her effortlessly fashionable style over the years, and her look perfectly demonstrated how the shoe can instantly elevate even the simplest outfit with ease
