Published September 25, 2026
It may be an urban myth that Anna Wintour has a lifelong dislike of polka dots, but Princess Eugenie certainly made a convincing case for the print during one of her most memorable style moments.
Long before her more polished recent looks, the royal was already proving she wasn't afraid to have fun with fashion.
One particular outfit from the 2010s has resurfaced as a reminder of just how distinctive her style was in her twenties - and it has plenty of charm even now.
At just 21, Eugenie attended the Epsom Derby in a monochrome mini dress covered in bold black polka dots.
The white dress featured capped sleeves and a flattering empire waist, while a wide black belt drew attention to her silhouette.
She continued the black-and-white theme with a chic straw hat and peep-toe stilettos, giving the race-day a polished finish without taking away from the statement print.
Even Eugenie's beauty look was firmly rooted in the era. Her brunette hair was noticeably darker than it is today, falling in long, glossy waves, while she opted for a dramatic smoky eye, warm bronzer and the quintessential nude lip.