9 Times Pippa Middleton's Wimbledon Outfits Seriously Stunned

Each June, the Wimbledon Championships kick off in London, attracting not only the best tennis players in the world, but the who's who across Great Britain, the United States, and beyond — and the fashion tends to garner as many headlines as the matches. If you delve inside Pippa Middleton's lavish life, you'll find that she's a regular at the buzzy tennis tournament, sitting alongside her royal family members and Hollywood celebs. Middleton is, of course, the younger sister of Catherine, Princess of Wales, but she's a published writer in her own right, having penned columns for Vanity Fair and authored a hosting how-to. 

We've had our eye on the stunning style transformation of Pippa Middleton. Her looks have gotten more refined over the years, but she hasn't abandoned the playful, feminine spirit that we've come to expect from her outfits. At Wimbledon, in particular, the British socialite seems to favor vibrant florals, bold prints, and classic silhouettes. Love.

When day 14 of Wimbledon in London in July 2024 commenced, Pippa Middleton was there in the stadium decked in an all-over floral print. She wore a maxi dress covered in a dreamy sea of dainty pink flowers and featured a darling little capelet. Middleton nipped in the waist with a ribbon-like bow and pulled her brunette locks back into a half-up, half-down style to complete a look that felt timeless and fun. Middleton's look is just one example of all the times women over 40 stole the show with their Wimbledon outfits.

Back in July 2015, Pippa Middleton swung by day 10 of Wimbledon in London looking equal parts funky and chic in a super of-the-era outfit. The younger Middleton wore a short-sleeved peplum top and a matching pair of skinny cigarette pants. The two-piece set was covered in a quirky black and white print that sort of reminds us of a Rorschach inkblot test — what does it mean if we see a stylish Brit? We're also loving the always-effortless aviator sunglasses. 

Pippa Middleton was in attendance for day 12 of Wimbledon in London in July 2019, wearing a frock that makes us think of the expensive china that might sit in an armoire you'd find in a sprawling English countryside estate — in the best possible way. The white fit-and-flare dress was decorated in a winding blue floral pattern with ruffled cap sleeves. The '90s sunglasses and the messy ponytail injected a bit of cool into a look that feels luxe, airy, and just the tiniest bit flirty.

To watch the matches on day seven of Wimbledon in London in July 2019, Pippa Middleton showed up rocking a powder-pink midi dress that was chic and simple, save for a couple of lovely details that added just the right amount of interest. We're looking at the longer sleeves that hit Middleton at the elbow, and the center pleat, which gave the thick fabric some movement and kept things from feeling too stiff. And, nope, we're still not over the nude mules, nor the cream-colored fedora. 

The Hollywood celebs must've rubbed off on Pippa Middleton, because when she showed up for day seven of Wimbledon in London in July 2017, she wore a look that was totally Los Angeles-approved. Middleton donned a mint-green off-the-shoulder dress that featured spaghetti straps, cheeky little folds at the bust, and tied side sleeves. She styled her hair in a '90s-era blowout and popped on a pair of beach-house sunglasses. And are we crazy, or does she look a little Megan Markle here? 

Pippa Middleton was among the crowd for day 11 of Wimbledon in London in July 2016, and the dress she chose was definitely fit for a royal — or, you know, the sister of a royal. For the game, Middleton opted for a dress in a luxe-looking fabric that was covered in a large, rich purple-floral print that was ultra vivid. We're loving the frock's ruffle detailing around the neck, button sleeves, and nipped-in waist. And Middleton's longer brunette locks were perfectly sleek and summery.

Pippa Middleton delivered one of her best fashion moments at Wimbledon's 2017 go-round. She showed up to the London stadium for day three of the championships wearing a delicate sheer dress crafted from intricately placed knit details. Small flowers, strips, and pearl-like dots came together for a dreamy pink patchwork. The white collar and black stripe at her waist were the perfect details to infuse a bit of masculinity into an otherwise deliciously dainty look, and the gray pointy-toe pumps and clutch were just right.

To cheer on the world's most elite tennis players on day four of Wimbledon in London in 2018, Pippa Middleton rocked a look that was as stylish as it was breezy. She chose a cotton-white dress that was etched in subtle, floral-printed stripes and featured super sweet ruffle-adorned straps. And, now for the fun part: Middleton topped off the simple dress with a wheat-colored fedora decorated with blue pom-poms, the same ones popular on tennis socks in the '90s, so, in other words, very on point for the event.

In July 2016, Pippa Middleton was in the stands for day nine of Wimbledon in London, wearing an above-the-knee sleeveless dress that may have been a simple A-line silhouette, but was crafted in such a fun fabric that it surely turned heads away from the matches. The shimmery pink material featured a peachy print of floating peacock feathers that reflected the sunlight — also seen in her dark sunglasses — in the loveliest way. And we're loving Middleton's undone hairdo with its playful face-framing strands.