Look Back at Pippa Middleton’s Chicest Style Moments

Positively posh! While being the younger sister of one of the most stylish women in the world (hello, Kate Middleton!) may have proven to be too intimidating for some, Pippa Middleton has established herself as a fierce fashionista in her own right. 

Whether it was her masterclass in maternity dressing (she shares son Arthur and daughter Grace with husband James Matthews) or her penchant for figure-flattering frocks and simply chic separates, the columnist and cookbook author has always had an eye for style. From designer gowns to affordable dresses, the mom-to-be has a classic-with-a-twist style that complements her super fit physique. 

Pippa established herself as a fashion force to watch shortly after her sister got engaged to the future king of England, leaning toward conservative silky designs with flattering silhouettes. But when the royal wedding rolled around in 2011, she exploded on the style scene, walking down the aisle in a curve-hugging Alexander McQueen maid-of-honor gown. 

The former party planner stunned just the same at her own wedding in 2017. For her nuptials to Matthews, she wore a custom Giles Deacon gown which featured a high neck, cap sleeve and long train. She accessorized her look with a Robinson Pelham tiara and a Stephen Jones veil. 

Pippa, an athlete in her own right, has also graced Us with fabulous fashion on repeat at Wimbledon — and her look is always a pattern party. 

She opted for a houndstooth Carolina Herrera matching set in 2015, a geometric Tabitha Webb number in 2016 and a striped Self-Portrait minidress in 2017. 

When the 2018 sporting competition rolled around, the author found herself sporting a new accessory: a baby bump! Pippa proved her maternity style would be unmatched, opting for a white eyelet dress, which she accessorized with a J.Crew clutch. 

The Marlborough College grad spent most of 2019 in floral frocks, before pivoting to chic outerwear around the holidays. While attending Christmas services in London, she looked spirited and chic in a green wool wrap coat — from Mango nonetheless. 

While Pippa wasn’t seen out and about too often in 2020 due to the COVID-19 pandemic, her 2021 style has been stronger than ever. For the Wimbledon tournament, she looked insanely stylish in a preppy gingham number by Ralph Lauren. 

To see all these looks and more of Pippa’s posh fashion, keep scrolling! Because from summery sundresses to high-fashion gowns and sparkly dresses, we’re rounding up her best looks of all time, below.  

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