There’s actual royalty... and then there’s Wimbledon royalty. And up in the Royal Box, the best seats in all of SW19, there’s frequently both.
Loyal followers of Wimbledon’s style files will know that certain faces are reliably chic dressers when it comes to courtside fashion, while others simply become one-hit wonders, never to be seen again.
The queen of courtside style is undoubtedly Catherine, Princess of Wales (aka Kate Middleton), who steals the show every time she appears in the Royal Box. Her potential presence this year is being hotly awaited following the Princess’s absence at Royal Ascot last month.
In the meantime, let’s reminisce on one of the best Wimbledon looks of all time: the year was 2023, and the Princess of Wales arrived at Wimbledon carrying one of the event’s official green and purple umbrellas. It handily matched her mint green and white double-breasted blazer by Balmain, which she had paired with a small purple bow tie and pleated white chiffon skirt. The whole thing was very reminiscent of Princess Diana circa 1988, when she visited Australia with a young Prince William and Prince Harry.
(Granted, this umbrella moment didn’t happen in the Royal Box, but Kate did later wear this outfit in the Box when she sat next to Roger Federer, who was looking equally dapper in a beige suit with a blue pinstriped shirt and polka dot tie.)
This was a great year for The Princess of Wales’s Wimbledon dressing, with Kate later donning a lime green skirt suit by Self Portrait and an emerald green dress by Roland Mouret. Matching the court is clearly Kate’s forte.
As for the king of Wimbledon style? Apologies to Prince William, but it’s actually Sir David Beckham, who is consistently the best-dressed man in Wimbledon’s Royal Box year on year. One of his best looks came in 2024, when the former England captain wore a sand-coloured suit, powder blue shirt, brown waffle knit tie and wayfarer sunglasses. Beckham’s prim Wimbledon style is offset by his many tattoos, giving an interesting edge to the otherwise buttoned-up event and its smart dress codes.
Unfortunately for David, Victoria Beckham doesn’t seem as keen on tennis, having only attended a handful of times, with Becks now routinely attending on his own. However, when she does show up, she shows off.
In 2014, the last year Victoria attended, she wore a V-neck colour block dress in shades of navy, maroon and orange, which came as a breath of fresh air amid the many pastel tones.
Another breath of fresh air came in 2018, when Meghan Markle arrived in the Royal Box alongside Kate Middleton, rocking a more androgynous outfit than you’d typically expect of a royal at Wimbledon. The Duchess of Sussex wore a navy and white striped shirt tucked into wide-leg cream trousers, with her hair in a low bun.
The next year, though, Meghan took it too far — or so the press thought. She arrived wearing blue jeans and was reportedly seated out of the Royal Box and away from the royal family due to the strict dress codes. The Daily Mail lambasted her behaviour as a “faux pas”. Two weeks later, the Duchess rejoined the Royal Box wearing a crisp white shirt and patterned plisse skirt. Lesson learned!
The Royal Box is also a prime seat for famous couples, who clearly enjoy dressing up for their tennis date days. Previous well-dressed attendees include Sienna Miller and Oli Green in 2024, who wore a polka dot dress and grey suit, respectively.
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Throw it back to twenty years ago, and you’ll find Sienna in the crowd with ex-husband Jude Law, wearing two outfits which are very clearly from 2004. The reigning queen of boho, Sienna wore a patchwork beige blazer with tiny plaits woven into her hair, while Jude was in his trademark open shirt and dark grey blazer.
Sienna has since become a Wimbledon staple, attending numerous times and often making headlines with her outfit choices. One memorable moment came in 2015, when she turned heads with her crisp white Galvan jumpsuit and bright red lip, a striking combination against the green of Wimbledon’s seats.
Another reliable attendee is former American Vogue Editor-in-Chief Anna Wintour, who (predictably) looks amazing at each Wimbledon appearance. One of her finest moments was in 2015, when the legendary magazine editor donned a grey and white floral dress embroidered with red petals and adorned with a black mesh layer at the skirt.
Two days later brought another brilliant Anna look, with the editor arriving in a ruched gingham dress and colourful jewellery, complete with a hot pink cashmere jumper tied around her shoulders.
All the best looks from the Wimbledon Royal Box throughout the years
