The ’90s were something of a golden age for footwear. From Carolyn Bessette-Kennedy’s pared-back Prada slingbacks to Carrie Bradshaw’s much-coveted Manolo Blahniks, the decade delivered some of fashion’s most memorable shoe moments. And, as with so many other aspects of the era’s aesthetic (coats, dresses and bags included), designers are looking back to the decade for inspiration this winter.
A sense of ’90s nostalgia was felt across the autumn/winter 2026 runways. At Dolce & Gabbana, classic leather Oxford shoes were styled with a checked skirt suit and sheer ankle socks in a preppy take on winter dressing. Elsewhere, the square toe ’90s shoe made a welcome return at Miu Miu, where brown satin pumps were paired with a straight-cut minidress, complete with a bow at the neckline.
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Few designers are as well known for a minimalist approach as Calvin Klein. For autumn/winter, the house brought back the pointed stiletto heel in ivory, styling it with a black satin high-necked tunic and midi-skirt that felt every bit CBK-coded.
Ever since Matthieu Blazy introduced his take on Chanel’s iconic cap-toe style, the design has become one of the most talked-about shoes of the season. Working just as well with sharp tailoring as they do with a favourite pair of straight-leg jeans, these are the cornerstone of an ’90s-inspired wardrobe.
Then there are the dancing shoes. Delicate, close-fitting, T-bar styles with a distinctly ballroom-inspired feel, these were another favourite of CBK, who styled hers with evening dresses, tailored trousers or simple slips when mingling with Manhattan’s elite.
Whichever way you lean, scroll on to discover the ’90s shoe trends worth knowing about this winter.
Oxford shoes
X Talia Byre Premium Real Leather Brogues
Square-toe shoes
Pointed stilettos
Two-tone shoes
