Pippa Middleton's 'breezy' Ralph Lauren dress and lace-up heels were her best pregnancy look


The Princess of Wales' sister was seen on day nine of Wimbledon in 2018 shortly before giving birth to her first child with James Matthews


Pippa Middleton in striped dress and sunglasses© Getty Images
Katie Daly
Katie DalyLifestyle Writer
March 30, 2026
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Pippa Middleton proves that the Princess of Wales' impeccable sense of style runs in the family – and that includes dressing a blossoming pregnancy bump. In 2018, Kate's younger sister, now 42, stepped out on day nine of Wimbledon with her brother, James Middleton.

At the time, she was six months pregnant with her first child, a son whom they named Arthur, and looked radiant in a shirt dress by Ralph Lauren. The linen number, which was perfect for the British July heat, featured an open collar neckline, as well as elbow-length sleeves and a tie-belt waist for a sense of structure.

Pippa Middleton in a striped Ralph Lauren shirt dress walking beside james middleton© Getty Images
Pippa Middleton opted for a Ralph Lauren shirt dress on day nine of Wimbledon

To keep her look cool, Pippa unbuttoned the floaty skirt slightly for extra movement. As far as her accessories were concerned, the wife of hedge fund manager James Matthews added a pair of black heeled espadrilles that laced up her leg and a crossbody bag to match. She also wore round sunglasses and gold hoop earrings for the ultimate off-duty look.

A stylist weighs in

Pippa Middleton in blue shirt dress sat in stands with james middleton© WireImage
Pippa Middleton's shirt dress kept her cool and stylish

Leanne Jones, a fashion stylist who trained at the London College of Style, tells us that Pippa highlighted how casual comfort is essential during pregnancy, but dresses offer a stylish option. 

"Similar Ralph Lauren dresses in the current collection are often made from breathable cotton, making them a great option for staying cool and comfortable," the stylist explains. "The cut provides plenty of room for the bump, while the loosely tied belt subtly defines the waist, keeping the wearer’s silhouette visible without compromising comfort.

Recommended videoYou may also likeWATCH: Pippa Middleton's sister Princess Kate's best Wimbledon fashion moments
Pippa Middleton in shirt dress with james middleton© GC Images
Pippa Middleton's shirt dress was a piece by the American designer Ralph Lauren

"It’s a perfect example of a breezy, effortless pregnancy look, and one I’d happily recommend as a textbook style for expectant mums."

James Matthews and Pippa Middleton at Wimbledon © GC Images
James Matthews and Pippa Middleton were seen arriving at Wimbledon for the Men's Semi Final Day

Two days later, Pippa made another Wimbledon appearance, this time arriving hand-in-hand with her husband, who is the brother of former Made in Chelsea star Spencer Matthews. The mum-to-be opted for another flattering summer dress, this time a £680 printed midi dress by Anna Mason.

Pippa Middleton in printed dress with james matthews walking© Getty Images
Pippa Middleton's Anna Mason dress skimmed her bump beautifully

It featured a tiered design and crew neckline and worked perfectly with the boho quality of her white heeled espadrilles and raffia clutch. Typically, Pippa's sister steers clear of casual espadrilles at Wimbledon, having only publicly worn a lace-up heeled wedge shoe on a handful of occasions over the course of her 15-year-long marriage to Prince William.

Princess Kate wears her Castaner wedge espadrilles with a printed midi dress to attend Cambridgeshire County Day at Newmarket Racecourse in 2022© WPA Pool
Princess Kate rarely wears espadrilles but they do feature in her summer wardrobe

This is most likely because a precedent was set by the late Queen Elizabeth, who was believed to dislike the style of shoe, and royal ladies were discouraged from wearing them in her presence.

Since making an appearance at the 2018 tennis tournament, Pippa has gone on to welcome two more children with James Matthews – Grace Elizabeth Jane, born in 2021, and Rose Louise Victoria, born in 2022. They live in a £15 million Georgian mansion in Berkshire.

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