Of all the many millions of photographs taken of Diana, Princess of Wales in the ’90s, those that show her en route from her car to the Chelsea Harbour Club are among the most indelible. Her signature combination of oversized sweatshirt, bike shorts and sunnies would go on to inspire a generation of It-girls – led by Hailey Bieber – who took to cosplaying as the People’s Princess as they made their way to Pilates around 2020.
Bieber and co have since moved on, but proof that the Princess’s look is an eternal source of inspiration popped up on the spring/summer 2025 runways, where ’90s-inspired sneaker boots – just like those Diana wore on her way to a workout – were paired with everything from minidresses to trench coats to tailoring.
Loewe, Christian Dior, Stella McCartney and Dior all included the trainer silhouette in their collections. In his final runway show before stepping down as creative director, Jonathan Anderson presented ankle-strap sneakers in shades of mocha brown and butter yellow at Loewe. Over at Dior, Maria Grazia Chiuri included silver and white sneaker boots in her sportswear-inflected collection. Stella McCartney made them office-appropriate with the addition of crisp tailoring, and Chemena Kamali styled them with boho minidresses and trench coats at Chloé.
Scroll down to see how designers – and fashion fans – are styling the ’90s sneaker boot for now.
