Pippa Middleton's Style Changed A Lot Since Kate's Wedding

The royal family and other British socialites are always photographed looking suitably well-dressed, whether they're attending an elite formal dinner or just moseying about. With Queen Elizabeth II, you could count on frequently seeing her sporting beautiful pearl necklaces or a well-designed hat, while with Princess Diana, her fashion sense often portrayed how the beloved royal felt. In other cases, some royals and royal associates may not have a trademark look because they like to shake things up now and then, like Pippa Middleton, the Princess of Wales' sister. While Middleton doesn't have a specific style, she often opts for a dress, with minimal jewelry and a natural makeup look. 

Sometimes, Middleton's choice of dress meets the needs of the occasion, but other times, she somewhat misses the mark, which often overshadows how well her hair is styled or the fact that her light makeup slayed. But how truly fascinating or disappointing have Middleton's fashion choices been? Here's what we've noticed over the years, starting with that incredibly chic showing at her older sister's wedding.

In 2011, William, Prince of Wales, and Catherine, Princess of Wales, tied the knot at Westminster Abbey. Though the wedding was memorable, Pippa Middleton's maid of honor dress rivaled even her sister Kate Middleton's wedding gown for media attention. Pippa wore a long, white, slim-fitting Alexander McQueen dress, expertly crafted out of satin and lace. Buttons ran down the back of the dress and additional fabric draped the neckline, creating an unexpected cowl neck. The dress's silhouette was narrow, highlighting her graceful curves. Middleton simply accessorized the dress with small earrings and added a hairpiece that held her half up, half down hairstyle, which stayed behind her neck, modestly exposing her décolletage. Nevertheless, the dress was so glaringly bright, that it looked like she had visited the Jersey Shore tanning shop.

In response to the attention the dress got, Middleton confessed to Today, "You know, I think the plan was not really for it to be a significant dress. Really just to sort of blend in with the train," she said. While the socialite considered the attention on the dress flattering, she also shared with Today that it was a bit embarrassing. She confirmed that the stunning gown remained in her closet and would stay there unless her children wanted to see it at some stage.

Between 2012 and 2015, Pippa Middleton was seen rocking bright colors and pops of patterns. At the 2012 U.S. Open tournament in New York City, she donned a mid-length, mid-sleeve, bright yellow dress, with her hair curled and bouncy. The dress was lined, had lacey patterns throughout, and was loose around her hips. The cheerful yet sophisticated feel of this frock could have made it a perfect option for a church service or a Wimbledon match (where most people connected to the Royal Family definitely wouldn't turn up in a t-shirt), but perhaps a touch formal for the U.S. Open. Granted, celebrities and elites dress well at these games, even if they aren't held at Wimbledon, but tend to lean more towards the "casual" end of business casual. A tennis bracelet and a more styled hairdo could have elevated the fit that somehow managed to be both overdone and plain at the same time.

However, the yellow shade worked in the socialite's favor in 2013 when she wore a mustard coat, and a big brown fur hat, paired with brown gloves to enjoy horse racing in Gloucestershire, England. Middleton never revealed what was under the coat, but the outfit screamed royalty. The mustard yellow coat complimented Middleton's skin tone, and her bone-straight hair matched almost perfectly with the Cossack hat. Since horse racing is more of an elite sport, this outfit combination worked perfectly, as opposed to the star's outfit choice for the 2012 tennis games.

By around 2016, Pippa Middleton often opted for more simple looks, which she executed well. In February of that year, Middleton attended the British Heart Foundation's Roll Out The Red Ball wearing a simple white mid-length, mid-sleeve dress with black detailing just above her elbows and on the dress's waist. She accessorized with a red, heart-shaped purse and red shoes, and wore her hair in a stylish side bun, with an intentional loose strand of hair in the front — she looked like a protagonist ripped straight out of the end of a Hallmark movie (which is a good thing!). In this case, it was Middleton's hairstyle and red accessories, including that perfectly lined red lip, that elevated the otherwise simple dress. 

The following year, Middleton rocked more white, but this time it was for her nuptials rather than a fundraising event. Pippa Middleton's wedding to James Matthews was not technically a royal one, but the ceremony and dress left pretty much nothing to be desired. Middleton chose a beautifully simple lace gown with a keyhole back, custom-made by Giles Deacon, paired with a custom pearl-encrusted veil, creating a timeless look. The dress fitted seamlessly above the bride's waist and lightly flared outwards to the floor. Her hair was tucked away from her face with twists and a chignon, leaving room to show off the high neckline of the dress, perfectly accentuating her height. The natural makeup and the small hanging earrings (the same ones she wore to her sister's royal wedding) were the icing on the cake, adding an extra touch of elegance to the bridal look.

By 2018, Middleton was expecting her first child and therefore understandably opted for maternity-friendly clothing, of which floral dresses seemed to be a favorite. Pippa Middleton gave birth to Arthur Michael William Matthews, on October 15, 2018. By 2019, the maternity clothes went out the window and the time came for Middleton to dip her toe back into some more fashion-forward clothing. Her first appearance after giving birth was at the 2019 British Heart Foundation ball where she donned a long, black, and multicolored dress that showed off her slim figure. The dress featured a black bow by the neckline, and the short sleeves were frilled. While the design above the waist of the dress is attention-grabbing, the belt line is quite high, making the bottom half of the dress fall slightly flat. Still, the dress's unique style and pattern, paired with the confidence Middleton wore it with gave the piece a fashionable edge.

The socialite subsequently stepped out that summer to enjoy tennis games at Wimbledon, wearing a pastel pink dress with a matching colored hat, a little smaller than the ones music producer Pharrell Williams would wear, and a clutch purse. Much like the yellow dress Middleton wore to the 2012 U.S. Open games, the look (which, sadly, is among the outdated outfits Pippa Middleton has been caught wearing) would have perhaps worked better for attending an upper-crust brunch or a similar event. Socialite dress codes at Wimbledon do sometimes veer more elegant and formal, but this particular look doesn't do much for Middleton. Her hair was also shaggy, which didn't match the aesthetic of the outfit she chose, leaving a lack of uniformity. If anything, the entire style made her look a little frumpy and slightly older than her years. 

During the 2020s, Pippa Middleton went through several types of styles, based on the season of her life she was in. Middleton gave birth to her second child, Grace Elizabeth Jane, in March 2021. In 2022, Pippa Middleton had big news to share with the world, announcing the imminent arrival of their third child, Rose, who was born in June of that year. She wore dozens of maternity-friendly outfits during those times, creating both classy and cute ensembles that ranged from sundresses and summer maxi dresses to more formal looks, including an exceptionally chic long-sleeved green dress worn to Princess Eugenie's wedding. The shade seems to be a favorite with Middleton, because in December 2023, at the British Heart Foundation's Heart Hero Awards ceremony, she wore a beautiful green cocktail dress, with nude undertones, paired with a red shoe. The dress, patterned with floral lace, was flowy and seemed to brighten Middleton's skin, giving her a radiant glow. The lightly puffy shoulders slightly aged the green gown but weren't a focal point since Middleton's loose bouncy hair distracted from it.

That same month, Middleton wore a red tweed suit with a black undershirt to a Christmas concert with her husband, James Matthews. The star wore light makeup and small earrings. This outfit was a refreshing change from the usual frocks Middleton opts for and created a sophisticated look.

Since her first inception into the public eye, Middleton's taste has morphed and matured to the point where she has become a style icon. Overall, the socialite has come to favor traditional looks, classic details, and feminine elements over trendy looks. But, she's also not above throwing in a bold color or unexpected print every so often!