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'90s shoes are making a comeback this winter - these chic, comfy styles are the ones to know, from £20

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Published on 2026-11-08 07:00:00
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'90s shoes are making a comeback this winter - these chic, comfy styles are the ones to know, from £20

It would be an understatement to say the ’90s gave us some of fashion’s most memorable shoe moments: Carolyn Bessette-Kennedy’s pared-back slingbacks, sleek pointed heels and simple flats that made an outfit feel instantly more polished.

But these styles aren't left in the past. This winter, ’90s fashion fans can rejoice: the decade’s understated approach is back, with styles appearing everywhere from the runways to the high street.

Square toe pumps

At Miu Miu this year, square-toe pumps made a welcome return, so the high street took note and have started to sell them in spades. The chic style adds structure to your outfit and looks especially sleek with tailored pieces.

Oxford shoes

Elsewhere, Dolce & Gabbana paired classic Oxford shoes with sheer socks for a preppy take on winter dressing. The boyish shoes is great if you're looking to add a masculine charm to your outfits.

Pointed high heels

Pointed high heels also appeared at Calvin Klein, bringing a chic, minimalist touch that felt unmistakably ’90s. We've found some great pairs that are very comfortable and nail the allure of the 90s office siren look. These courts also add polish to basic denim outfits.

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