Pippa Middleton's Best Wedding Guest Looks So Far

When you're part of British high society, attending fabulous weddings is part of the deal. The dress code for these events is slightly different from your average nuptials — think modest skirt lengths, hats that aren't too high, dresses that cover your shoulders, and florals year round. These guidelines leave room for interpretation (and some of the worst-dressed royal wedding guests of all time), but one person who nearly always gets it right is Pippa Middleton. 

The little sister of Catherine, Princess of Wales, Pippa was cast into the spotlight in 2011 when she served as the maid of honor in the royal wedding of the century. While her white bridesmaid's gown nearly stole the show, she's rocked numerous wedding-guest looks since that have earned her style points. If one thing's become clear with Pippa's fashion aesthetic in this time, it's that she likes to take a risk. Sometimes, she tiptoes a little too close to the edge of the rules, as she did at Arabella Musgrave's 2014 wedding when her oyster-cream dress, coat, and fascinator photographed as white. It hardly needs to be said that in our ultimate guide of what not to wear to a wedding, white comes in at the top of the no-no list. But we can forgive her for this almost-transgression when we consider her portfolio of other top-notch wedding-guest looks, from her prettiest pastel numbers to chic printed silhouettes — and, of course, that maid-of-honor dress.

In 2019, Pippa Middleton attended the nuptials of Lady Gabriella Windsor at St. George's Chapel. She was at the top of her game in a powder-blue dress from Kate Spade, which cost $738 at the time. Not only is the sophisticated hue of this dress ideal for a stately affair, but the details tell us everything about Middleton's power of intention. From the sheer, puffy sleeves that scream "Disney princess" to the floral print, belt, and buttons, this traditional frock could only be elevated by the addition of a perfectly placed velvet headband. 

Following her own 2017 wedding, Pippa Middleton became pregnant in 2018. She was nine months along by October, when she attended the nuptials of Princess Eugenie of York and Jack Brooksbank at St. George's Chapel, and she was a vision in an Emilia Wickstead forest-green midi. While florals and prints are standard for royal weddings, clearly solid colors can work too when done well. Middleton pulled this off by pairing the dress with black accessories and a bottle-green hat that served as the star of the show. Tonally, this look was also divine for fall without resorting to clichéd harvest hues. 

In 2011, Pippa Middleton was a global name after serving in the wedding of the Prince and Princess of Wales. A few months before she fell under the microscope of the world, though, she used her fleeting freedom to take a fashion risk at the February nuptials of Lady Katie Percy. Hot pink and black is always an eye-catching combo, but even more so when black is typically avoided by women at upper-crust weddings. Between the ruffles of her coat and the glimmers of vibrant pink in her Vivien Sheriff hat and Tabitha Webb dress, Middleton was clearly in her fun, single-gal style era.

Pippa Middleton attended a few weddings in 2018, the most famous of which being the St. George's Chapel ceremony of the Duke and Duchess of Sussex. Pippa appropriately went for florals for the spring event, expertly matching pastel tones of mint and blush in her Fold dress. The pleated hem saved this look from being a little too understated, and the floral hat made for the prettiest final touch. The strappy Jimmy Choo heels complemented the springtime look beautifully, and best of all, Pippa was twinning with mom Carole Middleton, who also wore mint.

When snaps emerged of Pippa Middleton from the 2013 wedding of James Meade and Lady Laura Marsham, we could have sworn we were looking at Kate Middleton herself. The blue lace dress from Tabitha Webb, which was somewhere between teal and lapis, evoked the Princess of Wales in her many teal-toned 'fits over the years. Both the dress and the Gina Foster hat were two-toned, and this, together with the side panels breaking up the lace of the dress, gave the look just the right amount of detail.

At the nuptials of Lady Melissa Percy and Thomas van Straubenzee in 2013, Pippa Middleton again played with fire in a Tabitha Webb dress that seemed to contain a lot of white. The black leafy print saved it from being a fashion faux pas, but only just. Wedding rules aside, this look was a winner for the fun peplum silhouette that was en vogue at the time, the creative feather-and-pearl hat from Olivia Roat, and the fact that the dress itself was tailored to perfection. All in all, this is even better than some of our favorite Kate Middleton wedding guest outfits. 

In theory, a black-and-silver dress paired with a pineapple coat that's embellished with metallic details could have been a disaster, but when Pippa Middleton attended Sam Waley-Cohen and Annabel Ballin's wedding in June 2011, she pulled it off against the odds. Admittedly, there is a sense of cohesion between the silver tones in the dress and the metallic cuffs of the coat, and the vibrant hue pairs well with the black Jane Corbett hat and shoes. Props to Middleton for even attempting such an experimental look, let alone landing it, at a time when the press was scrutinizing her every move. 

A lot of memorable moments took place during the 2011 wedding of the Prince and Princess of Wales, but among the most viral was Pippa Middleton's bridesmaid's dress. The satin ivory cowl-neck gown designed by Sarah Burton for Alexander McQueen had the world talking thanks to its snug fit, but it's the simple sartorial details that make this Pippa's best-dressed wedding-guest moment. From the lace-trimmed sleeves and neckline to the modest train, this gown was the perfect choice to accompany Kate Middleton's bridal gown down the Westminster Abbey aisle. 

Now, for more royal fashion, check out Pippa Middleton's stunning style transformation.