11 times Pippa Middleton stole the show at Wimbledon with her must-see outfits


The fashionista often attends with her sister, the Duchess of Cambridge


pippa middleton wimbledon© Photo: Getty Images

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Fiona Ward
Fiona WardContributing Writer
June 28, 2022

One of the reasons we love watching Wimbledon so much is the chance to see Pippa Middleton and her sister the Duchess of Cambridge show off their style credentials in the Royal Box.

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Pippa, who is reportedly pregnant with her third child, often attends with her husband James Matthews or brother James Middleton, and has even been spotted in the stands with Duchess Kate in the past. Keep scrolling to see all her most stylish looks over the years.

Pippa Middleton and another woman in sunglasses sit smiling among other spectators.© Photo: Getty Images

Back in 2012, Pippa and Kate attended the men's singles final together, looking gorgeous with their matching bouncy blowdries and chic outfits. Pippa wore a pretty peplum dress by Project D - the clothing label created by Dannii Minogue and Tabitha Somerset Webb – which has since closed.

She teamed it with a classic pair of sunglasses, while Kate wore a nude shift dress and carried a leopard-print Diane Von Furstenberg clutch bag. Wouldn't you love to see the sisters back together at Wimbledon?

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Pippa Middleton, wearing a black and white patterned jumpsuit, smiling and walking in a stadium.© Photo: Getty Images

Pippa wowed fans with her outfit in 2015, when she opted out of her usual floaty dresses and chose a gorgeous co-ord set from Carolina Herrera instead.

She finished the look with strappy wedges, a white clutch bag and a pretty braided hairstyle – a look we would later see her return to for another Wimbledon appearance!

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Pippa Middleton in a pink lace dress and sunglasses, walking down a street.© Photo: Getty Images

Her pastel pink Self-Portrait dress was another much-loved choice, worn during 2017's tournament while attending with brother James. The Duchess of Cambridge is also a big fan of Self-Portrait, as is the Duchess of Sussex and Princess Beatrice.

Pippa Middleton and a man in a beige blazer and blue pants holding hands while walking.© Photo: Getty Images

For 2018's appearances, a pregnant Pippa opted for cool, summery dresses – at the men's semi-final, she chose this pretty midi by Anna Mason, her trusty Ray-Ban round sunglasses and L.K. Bennett espadrilles. Her woven J Crew clutch bag is also a favourite of Duchess Meghan's, worn to a Sentebale polo match in later that month. She pulled her hair back into a braided ponytail, too.

Pippa Middleton in a white dress and blue shoes, walking with a hat in hand.© Photo: Getty Images

She also wore this gorgeous white lace dress during 2018's tournament, again by Anna Mason. This time, her wedge espadrilles were from Penelope Chilvers, and she also took a panama hat by royal milliner Jess Collett along with her.

Pippa Middleton in a green dress and sunglasses stands with friends at a stadium.© Photo: Getty Images

We love the simple off-the-shoulder dress that Pippa chose for day seven of the championships in 2017 – the pale green frock is by fashion label Tephi, and we could totally imagine Meghan wearing it, too!

Pippa Middleton in a white floral dress and sunglasses, walking with a man in a suit.© Photo: Getty Images

For another appearance during 2017's run, she looked stunning in this floral tiered maxi dress by Weekend Max Mara, and a green Tory Burch handbag.

Pippa Middleton in a white patterned cardigan and black skirt, holding a handbag, stands in a stadium.© Photo: Getty Images

Pippa went for a very classic look back in 2012, with this knitted Orla Kiely cardigan and navy blue dress.

Pippa Middleton in a black and white dress, smiling and standing with others in a stadium.© Photo: Getty Images

We could easily mistake Pippa for a smiling Kate in this beautiful monochrome floral dress! It's from Carolina Herrera, and Pippa wore it to Wimbledon in 2014.

Pippa Middleton smiling, wearing a floral dress and carrying a brown purse.© Photo: Getty Images

She went for a more relaxed look for another appearance in 2015, choosing this pretty floral number from another royal-favourite brand, Susannah.

Pippa Middleton in a pink floral dress and sunglasses, walking with a man in a blue suit and pink pants.© Photo: Getty Images

In 2019, Pippa went to watch the Men's Final Day at Wimbledon wearing a fabulous floral dress from Norwegian designer ByTiMo. She paired the frock with a pair of sunglasses from Finlay & Co., white open-toe heels and a matching white clutch bag.

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