The 5 Most Iconic Pippa Middleton Wimbledon Dresses & Her Latest 2024 Rewear That Sparked A Trend

Pippa Middleton, the younger sister of the Princess of Wales, has solidified her status as a quintessential figure of British summer style, particularly with her annual appearances at the All England Lawn Tennis and Croquet Club for the Wimbledon Championships. As of the current date, December 18, 2025, the most recent and talked-about outfits are her stunning selections from the 2024 tournament, where she showcased a masterful approach to high-low fashion by re-wearing a beloved piece.

Her style at Wimbledon is a carefully curated blend of royal elegance and bohemian chic, often featuring British designers, vibrant floral prints, and the perfect summer accessories like raffia bags and wedge heels. While her sister, Catherine, Princess of Wales, adheres to a more formal, tailored aesthetic, Pippa’s courtside looks are often bolder, more relaxed, and consistently trend-setting, making her a perennial subject of fashion commentary and inspiration for summer event dressing.

Pippa Middleton: Full Biography and Profile

Philippa Charlotte Middleton-Matthews, known universally as Pippa Middleton, is a British socialite, author, and columnist who rose to international prominence as the maid of honour at the wedding of her sister, Catherine, to Prince William in 2011. Her figure-hugging white dress at the ceremony became an immediate global phenomenon, launching her into the spotlight as a style icon and public personality.

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• Full Name: Philippa Charlotte Middleton-Matthews
• Born: September 6, 1983 (currently 42 years old)
• Place of Birth: Reading, Berkshire, England
• Parents: Michael and Carole Middleton
• Siblings: Catherine, Princess of Wales (older sister) and James Middleton (younger brother)
• Education: Marlborough College; University of Edinburgh (English Literature)
• Career: Author (Celebrate, Heartfelt), columnist for publications like Waitrose Kitchen and Vanity Fair, socialite, and event planner.
• Husband: James Matthews (married 2017), a hedge fund manager and former professional racing driver.
• Children: Arthur Michael William Matthews, Grace Elizabeth Jane Matthews, and Rose Matthews.

The 2024 Wimbledon Style Grand Slam: Rewears and Jumpsuits

Pippa Middleton’s appearances at the 2024 Wimbledon Championships were a masterclass in sophisticated summer dressing, demonstrating her commitment to sustainable fashion through re-wearing beloved pieces while also embracing bold new silhouettes. Her choice of attire for the Royal Box on Day 14, the Men's Final, was particularly notable, as was her earlier appearance in a striking jumpsuit.

The 'Peony Teaberry' Beulah London Dress

For the highly anticipated Men’s Singles Final, Pippa was seated in the Royal Box alongside her sister, the Princess of Wales, and her niece, Princess Charlotte. Her choice of outfit was a beautiful pink and white floral midi dress from the royally-approved British brand, Beulah London.

• Designer: Beulah London
• Dress Name: The Peony Teaberry Dress
• Key Details: The dress features a delicate pink floral print on a white background, a flattering midi-length, and a sophisticated silhouette with a cinched waist and short sleeves. It perfectly encapsulates the feminine and refined aesthetic expected in the Royal Box.
• The Rewear Factor: Crucially, this was a rewear. Pippa had previously donned the exact same Beulah London dress for her brother James Middleton's wedding in 2021, instantly earning praise for her commitment to mindful fashion.
• Accessories: She complemented the look with neutral accessories, often opting for her signature combination of chic wedge heels and a structured straw or rattan clutch bag, a quintessential summer accessory that adds a relaxed, textural element to her formal wear.

The decision to rewear a wedding guest dress for a high-profile event like the Wimbledon final was seen by many fashion critics as a powerful statement, aligning with the growing trend of sustainable style championed by many members of the royal family. The dress, with its "Barbie-pink" undertones, was also a subtle nod to the vibrant colour trend that dominated the summer of 2024.

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The Bold Floral Jumpsuit by Claire Mischevani

In an earlier appearance at the 2024 tournament on Day 12, Pippa ditched the traditional dress format entirely, opting instead for a striking floral jumpsuit. This choice was a bolder, more contemporary alternative that still adhered to the smart-casual dress code of the prestigious tennis event.

• Designer: Claire Mischevani
• Garment: A wide-leg, bold floral jumpsuit.
• Style Note: The jumpsuit featured a vibrant print and a tailored fit, showcasing her willingness to experiment with silhouettes while maintaining a polished look. This choice instantly differentiated her style from her sister's more conventional choices.
• Consistent Accessories: She paired the Claire Mischevani jumpsuit with her failsafe summer formula: a pair of comfortable wedge espadrilles and a J.Crew rattan clutch, proving that the right accessories can elevate any outfit, be it a dress or a jumpsuit.

A Decade of Courtside Fashion: Pippa’s Most Iconic Wimbledon Looks

Pippa Middleton’s style evolution at Wimbledon has been a fascinating journey, moving from playful prints to more structured, high-end designer pieces. Her consistency in choosing British designers and embracing cheerful summer colours makes her a perennial courtside style star. Her looks often feature a high concentration of topical entities, including specific designers and accessories, which contributes significantly to her topical authority in fashion media.

Here are some of her most memorable and entity-rich Wimbledon outfits over the past decade:

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1. The Pale Yellow 'Balmoral' Dress (2023)
In 2023, Pippa was spotted in a cheerful pale yellow dress by British designer Luisa Kelsey, reportedly named "The Balmoral." This look was a perfect example of her preference for bright, summery colours. She accessorised with chic sunglasses and a slightly wavy hairstyle, embodying relaxed summer elegance.

2. The Peppermint Green Telphi Dress (2017)
One of Pippa’s most celebrated looks was the cool, off-shoulder peppermint green dress from Telphi. Crafted from a breathable cotton blend, the dress was lauded for being both chic and practical for a warm summer day at the tennis. The colour was a fresh, vibrant contrast to the typical neutrals.

3. The Hydrangea Print Dress (2017)
Further solidifying her penchant for detailed florals, Pippa wore a light pink dress featuring a purple hydrangea print to attend Day 11 of the tournament in 2017. This look, often cited by fashion blogs, showcased her ability to wear busy prints without sacrificing sophistication.

4. The Orla Kiely Blue and White Dress (2012)
An early iconic look was her blue and white patterned dress from Irish designer Orla Kiely. She layered it with a matching blue and white cardigan and accessorised with a pair of Givenchy sunglasses, demonstrating her commitment to mixing high-street and high-end accessories. This look highlighted her early adoption of bold, graphic patterns.

5. The Red and Grey Tabitha Webb Dress (2015)
Pippa has frequently worn British designer Tabitha Webb, even collaborating with the brand previously. For a 2015 appearance, she chose a red and grey geometric print dress with a 1960s-inspired silhouette. She finished the look with a powder blue clutch bag, showcasing a subtle colour-blocking technique.

In conclusion, Pippa Middleton’s Wimbledon fashion choices, particularly her recent 2024 outfits, are a study in balancing classic elegance with modern trends. By championing British designers like Beulah London, Claire Mischevani, and Tabitha Webb, and strategically re-wearing pieces, she continues to be a powerful, influential voice in the world of courtside style, proving that true fashion authority comes from confidence and a strong personal style. Her consistent use of entities like raffia clutch bags, wedge sandals, and specific designers provides a masterclass in summer event dressing.