Princess Diana's Enduring Style: Cycling Shorts Trend

Princess Diana, nearly 29 years after her passing, continues to be a significant fashion icon. Her innate sense of style made every outfit she wore appear elegant and on-trend, with many looks still influencing fashion today.

One of her most enduring and humble styles involved pairing cycling shorts with oversized sweatshirts. While many associate such athletic wear with workouts, Diana made cycling shorts mainstream in 1995. She was famously photographed leaving a gym in orange cycling shorts and a boxy sweatshirt, a look that fans embraced.

Diana frequently wore cycling shorts in various colors, always with an oversized top, such as her recognizable 'Harvard' sweatshirt. This ensemble, nearly 30 years later, is still widely adopted. In 2024, Justin Bieber's wife was seen in Los Angeles wearing similar black cycling shorts with a bomber jacket and baseball cap.

Meghan Markle also paid tribute to her late mother-in-law in 2025 by wearing a Northwestern University sweatshirt, reminiscent of one Diana wore in 1996. Princess Diana had previously paired a college sweatshirt with cycling shorts and trainers in London, showcasing a style that remains influential.