Pippa Middleton's red hot Wimbledon debut in daring dress sister Kate 'wouldn't wear'


Princess Kate's sister wore a daring £129 dress by Hobbs London to Wimbledon in 2011 - the first time she was photographed at the famed sporting event


© Corbis via Getty Images
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Laura SutcliffeFashion and Beauty News Editor
Rachel AveryHomes Editor
Updated: July 3, 2026

Pippa Middleton, just like her sister, the Princess of Wales, has always been a longtime tennis fan. The mother of three told Vanity Fair in 2013: "I first went to Wimbledon when I was eight years old and already a very keen tennis player."

Recalling the first time she went to the All England Lawn Tennis & Croquet Club, she further remarked: "During this first trip, I acted on my childish tennis dreams and bought myself a postcard of the women's championship trophy, on which I wrote, 'I will win this one day,' with my signature below."

Pippa Middleton and James Middleton attend day one of the Wimbledon Tennis Championships at Wimbledon on June 27, 2016 in London, England. © WireImage
Pippa has said she first went to Wimbledon at the age of eight

Pippa's public debut at Wimbledon, mere months after her sister Kate married Prince William, came in 2011. Arriving with her then-boyfriend, Alex Loudon, Pippa looked happy and relaxed as she took her seat next to the former cricketer, wearing a resplendent red dress. 

Carole and Pippa Middleton laughing at Wimbledon© Getty
Pippa made her public Wimbledon debut in 2011

It came from luxury high street store Hobbs London, costing £129 at the time of purchase, but it quickly sold out after Pippa was seen in it.

This dress, which was designed in a shift shape, with capped sleeves and statement button detail, was quite the chic style, and the tomato red shade was bold and eye-catching. The playful, above-the-knee hemline offered a more relaxed silhouette than the modest, midi lengths the Princess of Wales typically favours for royal appearances.

Pippa wore the 'Wyldes' dress by Hobbs London, which has a mini hem© PA Images via Getty Images
Pippa wore the 'Wyldes' dress by Hobbs London, which has a mini hem

The royal hemline rule

Royal style rules dictate that working female royals should stay away from miniskirts and keep hemlines modest and respectable. 

Kate in printed green midi dress© Getty Images
The Princess of Wales mostly wears midi skirts and dresses

These rules have been subtly defied by some over the years, but Kate has stayed pretty loyal to this style expectation.

Pippa and Kate's early Wimbledon memories

In the same Vanity Fair interview, Pippa recounted a time that she and Kate queued for cut-price Wimbledon tickets, recalling when she queued "from five a.m on 'People's Sunday' in 2004 with my sister for three hours and getting £35 tickets on Centre Court; my first time ever," she noted.

A photo of Kate and Pippa Middleton© Getty Images
Pippa and Kate are huge Wimbledon fans

"Seats were a free-for-all," she remarked, "and I recall almost tripping over myself trying to get as close as possible to my birthday-twin British hero Tim Henman."

Pippa Middleton's hottest looks over the years

Plunging fairytale dress© Getty Images

Princess Kate's sister wore a nude-hued maxi dress

Plunging fairytale dress

Pippa stunned at The Royal Parks Charity Gala at the Serpentine Lido in Hyde Park in 2008, sporting a plunging maxi dress with an embellished empire line.

A photo of a brunette woman wearing a purple dess© FilmMagic

The dress hugged Pippa's figure

The mini dress

In 2011, Pippa was strolling to the shops in a form-fitting mini dress which showcased her sport-honed figure perfectly. 

Pippa Middleton coming into venue in black gown© Getty

Pippa went for a sheer skirt

Sheer dress

Pippa Middleton glammed up for the Sugarplum Ball at One Mayfair in 2013, showing us that a classic black dress is always a winner. The cut out lace and sheer skirt make it oh-so sultry.

Pippa Middleston walking away from red carpet in black dress© Getty

Pippa rocked a monochrome dress

Bodycon dress

A classic look of the era, Pippa Middleton wore a bodycon mini dress to attend the UK Film Premiere of 'Shadow Dancer' at Cineworld Haymarket in 2012. The monochrome number, simple accessories and glossy locks were all about looking preened and polished.

 Pippa Middleton attend the inaugural Roll Out The Red Ball in aid of the British Heart Foundation at The Park Lane Hotel on February 10, 2015 © Getty

Pippa was the lady in red

Red dress

Ensuring she was red hot for the occasion, Pippa arrived at the Roll Out The Red Ball for the British Heart Foundation in 2015 in a striking postbox hue. She went one step further and teamed her dress with red heels for a double whammy. 

 Pippa Middleton attends a donors dinner hosted by Michael Bloomberg & Graydon Carter to celebrate the launch of the new Serpentine Sackler Gallery designed by Zaha Hadid on September 24, 2013 in London, England. © Getty

Pippa looked stunning in this striking dress

Feathered dress

Pippa turned heads in a dress that wouldn't look out of place on the Strictly Come Dancing dancefloor, complete with above-the-knee hemline and layers of fabulous feathers. Kate's sister was out to admire the new Serpentine Sackler Gallery designed by Zaha Hadid in 2013. 

pippa middleton white dress© Photo: Getty Images

Pippa got the Wimbledon whites memo

Wimbledon whites

To attend Wimbledon in 2018, Pippa nailed the chic Wimbledon whites look with a lace dress featuring detailed capped sleeves. Although not her sexiest look to date, we think the angelic white and fashionable silhouette make it white hot. 

pippa middleton1© Photo: Rex

Pippa wore a floral sundress

Feminine florals

Showcasing her perfect pins, Pippa wore a floral sundress as she left her home in Chelsea in 2016. But, at the time, all eyes were on the Asscher-cut diamond on her finger as she had just announced her engagement to James Matthews. 

Pippa Middleton © Photo: Rex

Aqua blue looked fabulous on Pippa

Ballgown beauty

Channeling a Disney Princess, Pippa slipped into an ice-blue ball gown by Hugo Boss for the ParaSnowBall 2015 - and it worked perfectly with her gorgeous tan!

kate pippa wedding© Photo: Getty Images

Pippa's dress garnered a lot of attention at the Royal Wedding

That bridesmaid dress

it wouldn't be a complete list without mentioning that iconic bridesmaid dress which she wore for her sister, Princess Kate's 2011 wedding day. The immaculate fit and elegant cut made it a dress to remember. 

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