Princess Diana's Wimbledon Fashion Moments Ranked By Timelessness

Princess Diana was a major tennis fan. Like many athletic aristocrats, she played the sport, but she was also a fixture of the Royal Box at Wimbledon as early as 1981. Fashion at Wimbledon is serious business, and Diana flexed her prodigious style credentials when she attended the iconic matches.

Wimbledon defines its dress code rather vaguely as "smart casual." Spectators are specifically prohibited from wearing clothing featuring political, offensive, or commercial prints. But while the attire might not be explicitly defined, there's a distinct aesthetic that is expected from spectators, especially in the Royal Box. "When you think about Wimbledon dressing, everyone has the same kind of thing in mind — either white or beige," sport and fashion journalist Daniel-Yaw Miller told the BBC. "You wear a blazer, you can wear a hat."

Diana's Wimbledon fashion game was strongest when she leaned into expressing her own taste. Her outfits reflected such a clear sense of self that Diana deserves her own fashion aesthetic. She put her own sense of sportiness and playfulness into the country wear-meets-prep school "Sloane Ranger" style that was popular with many upperclass British women of the era. It also happened to make for the perfect Wimbledon wardrobe. "She had such a fun and interesting style, wasn't afraid of bright colors or cuts that are a bit risqué, but also does the proper posh lady thing extremely well," wrote one Reddit user.

Princess Diana embraced a bold red moment at the 1994 Men's Single Final when she stepped out in a sleeveless collared dress. Both the enormous gold buttons and military-inspired pockets date this piece to a specific early '90s posh aesthetic, especially when paired with chunky gold jewelry from Tiffany's & Co. like Diana did here. In addition to looking dated, the bright red color is a surprising misstep from Diana, who usually had a knack for picking outfits that flattered her Light Spring color palette.

The enormous Peter Pan collar that Princess Diana wore for the 1987 final immediately dates this dress and not in a good way. Since, by this time, Diana had already embraced power dressing, this demure gown feels like an odd return to her younger, girlish style. Additionally, dresses with Peter Pan collars did enjoy a revival in the '90s, largely because the grunge movement embraced them. But Diana is wearing this one without a trace of apparent irony, which just leaves her looking like she's stuck in the '60s.

Princess Diana nailed Wimbledon style in 1981, when she appeared in the Royal Box wearing a particularly demure look, featuring a ruffled dress and quilted jacket. This look, which evokes the softer, feminine styles of the late-'70s, could easily pass for contemporary cottagecore style. But it feels disconnected from the bolder style that Diana embraced as she came into her own later in life, and lacks the timeless personal style element of many of her other Wimbledon looks.

Princess Diana was all '90s power dressing when she stepped out at Wimbledon in 1991 wearing a dark blazer over a patterned dress. Like so many of her outfits with blazers, the heavy gold buttons do much to date the look. Still, her accessories are more restrained here, making the overall outfit reasonably timeless. Most of all, she looks comfortable in this look, and an outfit that makes the wearer look more like herself is always in fashion.

For the 1993 final, Princess Diana wore a relaxed peach suit with bold gold buttons. Despite the fairly neutral silhouette, the metallic buttons immediately place this as a mid-'90s look, particularly in tandem with Diana's button earrings and gold choker, making it a bit less timeless. Despite that, this look is an enduring success because it's such a perfect embodiment of Diana's aesthetic — her own sporty, opulent spin on power dressing. After all, personal style is timeless.

Princess Diana wore a smart pastel skirt-suit to Wimbledon in 1995. There were certainly some late-'80s and early-'90s references visibly present, with its sharply structured shoulders, oversized buttons, and three-quarter-length sleeves. Still, the matching set with its nipped waist is undeniably classic. Plus, considering that butter yellow is the on-trend color you should add to all your outfits even now, it's clear this is a shade that stands the test of time.

In evaluating the timelessness of each look, the colors, silhouette, and accessories were all considered. Outfits that felt dominated by the trends and styling of a particular era's aesthetic were deemed to be less timeless than outfits that were harder to pin to a specific time period. Since personal style is particularly timeless, outfits that embodied Diana's unique sensibility were placed slightly higher than looks that felt more generic.