Awkward Pippa Middleton Moments That Were Caught On Camera

These days Philippa Middleton Matthews, known to the world as "Pippa," appears to lead a quiet life of posh respectability. She describes herself as an "author, columnist, socialite and younger sister of HRH The Duchess of Cambridge" on her Instagram account, where the faces of her three children in vacation pics are dutifully blurred. Some might attribute this reticent public demeanor to a contented life with her husband James Matthews, the chief executive of the hedge fund Eden Rock Capital Management Group.


Yet there was a time just before her 2017 marriage — during the roughly six years following her maid of honor cameo at Kate and Prince William's 2011 wedding — when Pippa seemed to regularly bumble into one awkward situation after another, each recorded by nearby cameras and posted online. Often these pics and video streams were accompanied by gossipy, insinuating headlines in bold print. 

You can imagine that for her it probably felt like the press was some collective "mean girl," waiting to humiliate and embarrass her. So how did she handle having so many uncomfortable moments immortalized online? 

The Wimbledon moment that wasn't

Think back to Wimbledon 2016. Pippa Middleton Matthews seemed to relish watching the match while holding up her end of a relaxed conversation with her brother, James Middleton. Yet, as Entertainment Tonight described it, Pippa "nearly flashes Wimbledon crowd in super short dress." What had actually happened? Pippa, who wore a lightweight, white dress with a floral design, had simply tried to straighten her twisted skirt while remaining seated, which, as anyone who's ever worn a summer frock understands, is a difficult task to do gracefully. 


For Pippa, this inelegant moment was captured in a photograph, that headline writers tried to turn into something it wasn't: an embarrassing bid for sexual attention. But context, as they say, is everything: Look at additional photos run in the Daily Mail and you'll see that her dress was actually knee length. She didn't deserve the salacious headline for either the choice of dress or the maneuver to straighten it. 

Pippa, rightfully so, laughed off the incident.

Book launch

In 2012, Pippa had a book launch incident. Her book, "Celebrate: A Year of Festivities for Families and Friends," is a collection of simple recipes and creative tips for commemorating holidays and other occasions. Divided into four seasonal sections, the book includes a cornucopia of photographs. The first-time author worked as an event organizer at the time and wrote with a playful spirit about decorations, children's activities, and British customs.


When presenting her newly-published book at a shop in Fulham, she joined a children's crafts party. As the girls and boys cut colorful construction paper and squeezed copious amounts of Elmer's glue onto the table, Pippa gamely tries to pull them into a conversation. "I bet when you're 10 you'll love pink and you'll love princesses," said Pippa, as captured by The Telegraph. One girl, wearing face paint and red devil's horns, pipes up: "I hate princesses!" Tickled, Pippa immediately answers, "Better not talk about that one!"

Royal wedding fame

Pippa's sense of humor in the face of unasked-for publicity dates back to the very first time international media ensnared her. In fact, it all began on a sunny April day in 2011 when she arrived at Westminster Abbey wearing an Ivory Alexander McQueen gown that clung to her curves like a Monaco Grand Prix race car. Pippa's role as her sister's maid of honor called for her to carry the long train of Kate's (related) Alexander McQueen gown, and so she bent to prevent the beaded gown from dragging the pavement. 


Unknown to her, images of her backside had circled the globe on TV screens and social media feeds before she even left the abbey. 

Months later, various media outlets still refused to let it go. Witness the HuffPost article from that period, subtitled, "A Year In The Life Of Pippa Middleton's Bum."  Pippa, herself, was never so rude or so crude. In "Celebrate," she wrote: "It's a bit startling to achieve global recognition (if that's the right word) before the age of 30 on account of your sister, your brother-in-law, and your bottom."  At her core, she's always been the tasteful woman glimpsed today — not just a sister to the crown, but an honorary "Lady," who could receive a new title for this surprising reason.