Pippa Middleton is the ultimate Chelsea girl in striking silk dress alongside sister Princess Kate


The Middleton sisters have always had exquisite taste and these photos from their Chelsea girl days are the proof. See photos.


Image© Getty Images
February 13, 2026
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Pippa Middleton has a stellar sartorial reputation, but while we fawn over her exquisite collection of immaculate coat dresses and Erdem gowns of recent years, her Chelsea girl years certainly merit equal appreciation. 

Cast your minds back to 2007, the now Princess of Wales was in the rockier months of her relationship with her university beau, Prince William, and the sister duo were living it up in a £1.8 million flat in Chelsea.

A photo of Pippa Middleton and Kate Middleton© Getty Images

For the occasion, Pippa chose a plunging satin gown in butter yellow adorned with black and colourful flowers. She paired the look with killer black heels and an of-the-era capped sleeve shrug.

Kate looked equally as fabulous for the outing, wearing a champagne-hued lace gown complete with black patent peep-toe heels. Both sisters opted for the ultimate noughties glam, meaning black kohl liner was on the menu. 

Pippa looked gorgeous in a butter yellow gown© Getty Images

As for hair, Pippa had her short, choppy layers styled immaculately straight, while Kate echoed the lengthy look, but flipped her locks to one side for a very 2000's side parting. 

Despite the photo being nearly 20 years old, you cannot deny their fashionista prowess, which has only gotten better with time. 

But their jaunt in 2007 wasn't the only time they were pictured living their best Chelsea girl lives. 

A photo of Pippa Middleton wearing a black skirt© UK Press via Getty Images

Another throwback favourite has to be when a flawlessly sun-kissed legs. Taking her Chelsea-girl style to Northumberland, Pippa headed off to a wedding at St Michael's Church in Alnwick.

For the occasion, she sported a black rara coat dres,s which she wore over a hot pink gown. Flaunting her tanned legs, not forgetting the matching hot pink fascinator she added to complete the killer look.

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

Meanwhile, strutting along the King's road was never off the table when it came to the Middleton sisters. One spectacular sartorial moment saw Pippa in 2011, making her way along the perfectly paved roads in SW3.

The outfit in question was a fabulous waist-cinching dress in a lilac hue and adorned with white flowers. Pippa was the toast of the King's road, completing her ensemble with a pair of silver cork wedges, which she matched with her silver handbag.

Pippa Middleton wearing a halterneck silk gown© UK Press via Getty Images

As for evening wear, Pippa always knew how to turn up the glamour, and the proof was in the pudding when she attended the Berkeley Square End Of Summer Ball in 2008. 

Stepping out in a silk halterneck ensemble of dreams. The tanned beauty completed her look with the ultimate pair of noughties killer heels: white satin and covered in diamantes.

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