The Best Royal Ascot Fashion Moments Over The Years

Each year for the last 300 years, the royal family has gathered together in June at the Berkshire racecourse for the annual Royal Ascot. Founded by Queen Anne in the 1700s, the week of races has turned into more than just a thrilling display of world-class thoroughbreds. Over the last few decades, it has become the ultimate summer runway where creative expression meets tradition, especially considering the specific Royal Ascot rules attendees have to follow. 

The royal family themselves are the best at keeping this delicate balancing act. Decade after decade, figures like the Princess of Wales and the late Princess Diana have flawlessly honored the race event's etiquette — all while still showcasing posh looks that have gone down in style history. Let's look back at the archive of style to spotlight some of the best Royal Ascot modern looks, starting from the '70s. While it'd be amazing if we could highlight all of the best fashion moments, in doing so, we'd end up with an endless stream of outfits.

Like many other guests, Kelly Osbourne managed to stay true to her signature rock 'n' roll style at the 2026 Royal Ascot and looked fabulous doing so. However, the royal family favors the rulebook over trackside glamour ... at least most of the time. There's always a rebel in the family who completely tears up protocol, proving that sometimes royals can't help but break the mold and look fabulous while doing so.  

In 1970, Queen Elizabeth II and her daughter, Princess Anne, showed up to the races in outfits that felt coordinated, yet uniquely individual. Princess Anne was seen fully embracing the '70s tailored aesthetic in a structured butter yellow coat and matching hat that hangs elegantly around the crown of her head, showing off its unique structure. Her mother perfectly anchored the moment in a pristine white coat layered over an olive green and white tweed pattern dress, all accessorized with a hat that complements the look dashingly. 

Princess Diana was photographed in the royal enclosure at the 1986 Royal Ascot, looking stunning in a head-to-toe all-white ensemble that perfectly captured her bright, graceful essence. The princess opted for a two-piece skirt suit that featured a beautifully pleated jacket cinched at the waist with a crisp pencil-style skirt. Even her accessories, such as her wide-brimmed hat and choker-style pearl necklace, were white. With this daring choice, she proved that even when lacking color, she would always stand out from a crowd.

It shouldn't be a surprise that Princess Diana is on this list twice. In fact, she would have made the list again if she were still with us today. For the second day of races in 1990, the princess proved you didn't have to wear busy patterns to make a statement. She donned a striking pastel pink skirt suit that was perfectly tailored to the tee and featured vibrant purple clashing accents on the lapels, pockets, and buttons. This elegant two-tone look confirmed Lady Di had mastered color block dressing.

Princess Anne rejected royal titles for her children, but that doesn't mean Zara Tindall is any less noble, so she's a familiar face at Royal Ascot. Without a title, though, Phillips gets to dress as she pleases for the annual races. That freedom gave us her iconic 2003 look. While the dress fell appropriately at the knee, the details were anything but traditional: a high slit showing off her toned Olympian legs and a one-shoulder neckline that bared more skin than any royal family member ever had in Royal Ascot history.

By the 2010s, Royal Ascot's guests were dressing in the most untraditional, attention-grabbing ways possible, but not Queen Elizabeth II. You could always rely on the late monarch to keep things modest yet delightfully vibrant, and the 2019 edition of Royal Ascot wasn't the exception. For this event, the queen looked adorably elegant as she wore a floral dress under a pastel blue coat with gold button details. The best part? The purple and blue floral details on her hat matched her dress pattern perfectly. 

We love it when the ladies of the royal family embrace lively colors, and you can trust the Princess of Wales to channel a bold hue with sophistication. Just like when Kate Middleton gave the butter yellow an elegant upgrade at Garter Day 2026, she showed up to the fourth day of the 2023 Royal Ascot exuding Spanish muse vibes. She wore an Alexander McQueen midi dress featuring a plunging neckline. The look felt like it was inspired by flamenco dancers as she was in fiery red from head to toe.

Sometimes, letting your bling do the talking is the ultimate fashion strategy. For day two of the 2026 Royal Ascot, Queen Camilla wore an all-white look, keeping it anything but modest thanks to a diamond brooch. The floral brooch, which was custom-designed by Cartier in the '50s for Queen Elizabeth II, made Queen Camilla's outfit all the more dazzling. By wearing all white, she let the diamond really shine and take center stage.