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Pippa Middleton watching the tennis on day four of the Wimbledon Lawn Tennis Championships at the All England Lawn Tennis and Croquet Club at Wimbledon on June 24, 2014, London, England.© Corbis via Getty Images

Pippa Middleton's 'elegant' party dress is the daring look of Wimbledon 2025

The wife of James Matthews gives us a lesson on Wimbledon dressing…

Laura Sutcliffe
Fashion and Beauty News Editor
June 30, 2025
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Wimbledon 2025 is here, and we are so excited for the world's most famous tennis tournament to officially get over the net.

Fashion and dressing elegantly are always at the forefront of the iconic event, and although there isn't a specific dress code, smart attire is always appreciated and welcomed.

Pippa Middleton, the sister of the Princess of Wales, is a longtime tennis fan, just like her royal sibling, and frequents the tournament, year after year.

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Pippa Middleton wearing a retro mini dress at Wimbledon in 2016© GC Images

Although it's hard to pick a favourite look (we'll move on to her array of outfits later), there is one dress she donned in 2016 that was rather daring, and we can't stop thinking about it, even now, all these years later.

That year, the mother-of-three took her seat to watch tennis legend Roger Federer in action from the Royal Box at Centre Court that year, rocking a mini dress by high-end designer, Tabitha Webb.© WireImage

Pippa's vibrant frock attracted many admiring glances, as it was designed in an orange and grey colourway, with a vintage, 70s-style geometric print to boot. The almost psychedelic number was still charmingly elegant and respectable, as it had a high neckline, was light and airy, and offered the brunette beauty some coverage from the hot sun, too.

Anna Wintour sat in front of Pippa Middleton at Wimbledon in 2016© WireImage

Keeping the rest of her look simple, the brunette beauty added a sleek clutch bag by Kiki McDonough and classic heels, letting her straight hair waft in the breeze, sporting minimal makeup. First class.

Also during that appearance at Wimbledon, the then 32-year-old shared a box with US Vogue editor Anna Wintour, who sat a few rows in front of Kate's sister. Legendary.

Pippa Middleton court-side of Centre Court© Karwai Tang

Pippa's best Wimbledon looks

In 2024, Pippa wowed at the world-famous Grand Slam championships, wearing a beautiful floral dress from a royally loved brand, Beulah London. Pippa's dress had an elegant full-length skirt, a contrast waist belt, and angelic flutter sleeves.


Wimbledon: 5 surprising facts

Media Image© AFP via Getty Images

1. A lot of tennis balls 

Throughout the tournaments, Wimbledon goes through over 50,000 tennis balls! After the first seven games, the balls are replaced and refrigerated to maintain bounce. 

2. Strawberries and cream

Tennis and strawberries are never apart throughout Wimbledon, and in fact, they only get the fruit from one supplier. Last year, Hugh Lowe Farm in Kent provided around 1.5 million strawberries over the two-week tournament. 

3. Rufus the Hawk

Rufus, the hawk, has been the protector of the Wimbledon courts for the past ten years. He flies above the grounds in the early AM to chase away any pigeons to maintain a pristine court condition. 

4. Prize money 

The winners of the ladies’ and gentlemen’s singles championships will each receive £2.2 million. Additionally, the winners of every round will also receive money, ranging from £1500 for the winner of the first round of mixed doubles, up to £1.1 million for the runner-up in the final.

5. Longest match in history

In June 2010, John Isner and Nicolas Mahut battled for 11 hours and 5 minutes over three days, with the longest match in professional tennis history. The match totalled 183 games, and John eventually won 70-68. 

Pippa Middleton in a turquoise suit© PA Images / Alamy Stock Photo

Also that year, Pippa watched a match between Italy's Lorenzo Musetti and Serbia's Novak Djokovic wearing a gorgeous 'Mimi' jumpsuit from Claire Mischevani.

The jumpsuit featured a cinched waistline and flared wide-leg trousers. The garment also had short bell sleeves and an open neckline with buttons down the front. A total 70s siren.

Pippa Middleton wearing pink floral dress© Getty

In 2019, Pippa graced the Royal Box, looking radiant in a candy-pink tiered dress adorned with vintage florals. It boasted a deep 'V' neckline and went magnificently with her bronzed suntan.



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