Pippa Middleton's Gorgeous Hair Transformation Through The Years

Ever since she first rose to prominence as the sister of Catherine, Princess of Wales, Pippa Middleton has wowed as an impeccably fashionable it-girl. But none of Pippa's iconic sartorial moments would be complete without her hair. The socialite-turned-author has been blessed with some of the most enviable celebrity tresses: impossibly lustrous, bouncy, and never with a strand out of place. Pippa may never ascend the throne, but she reigns as queen of the coiffures.

While Pippa Middleton isn't immune from wearing a shocking outfit or two, her hair game has always been A+. Throughout the years, the star has experimented with a surprising number of 'dos before finally finding her signature style. "Pippa switches up her hair color and hairstyles regularly meaning she's always sporting a fresh new look, but it's all within reason — and never too drastic ... For every amazing Pippa Middleton hair moment, there's an equally good style one to go with it," hair stylist Inanch Emir told Express. It's Middleton's willingness to embrace change that makes her a particularly appealing addition to many a Pinterest hair-inspo board. Let's run through Pippa's gorgeous hair transformations through the years.

Pippa Middleton has undergone a stunning transformation from Y2K party girl to demure socialite sister of the Princess of Wales. Back in 2007, she found herself in the public eye due to Catherine's on-again-off-again relationship with Prince William, which the younger Middleton sister was reportedly instrumental in rekindling. Attending a number of trendy events that year, Pippa was already making waves in elite social circles and cementing her status as a society it-girl. "Kate and Pippa have already been dubbed The Wisteria Sisters — they're highly decorative, terribly fragrant and have a ferocious ability to climb," a source told the Daily Mail at the time.

Appearing at the launch of the book "Young Stalin" by Simon Sebag Montefiore, Pippa wore her simple chestnut locks down. Typical of the aughts, her hair was super sleek and straight with minimal styling, which is in stark contrast to the pristine blowouts that have come to define Pippa's later approach to haircare. 'Twas a simpler time.

Prince William and Princess Catherine's 2011 wedding was the royal event of the year. But while Catherine was a stunning bride, it was her sister who ended up stealing the show. Pippa Middleton went viral at the Princess of Wales' wedding, both for those derrière pics — the virality of which was arguably a product of a sexist culture intent on reducing women to the sum of their parts — and her iconic maid of honor hair.

Pippa wore her hair in a half-updo with cascading curls secured in place by a dazzling floral hair clip. It was undoubtedly one of Middleton's most memorable moments, securing her status as a hair inspo queen. Speaking to the Daily Mail at the time, her hairdresser, Richard Ward, offered some tips on how us mere mortals can get hair as lustrous as the maid of honor. "Leaving any cut any longer than 12 weeks will result in dry, scraggy ends with no style definition that just gets harder and harder to look good," he offered. Seeing Middleton's pristine tresses is enough to make even the most salon-phobic folks book that haircare session.

By 2012, Pippa Middleton was moving away from her party girl persona and pursuing ventures close to her heart. Seeing as her parents owned a successful party supplies business (Party Pieces, which went into administration in 2023), Middleton knows a thing or two about party planning. Accordingly, she released her book, "Celebrate: A Year of Festivities for Families and Friends," which offered tips on everything from creating Halloween costumes to how to organize a successful Easter egg hunt.

Appearing at her book launch in London, Middleton went for a daring new 'do. A world away from those tumbling dark locks, she wore her hair in a retro, '60s-style updo, complemented by a smokey eye look. It was a dramatic change for the socialite, but a welcome one. Grazia argued that Middleton's willingness to experiment with bolder hairstyles proved that she was more adventurous than her big sister, Princess Catherine. However, rocking such eye-popping hair would be incongruous with Catherine's effortlessly classic approach to royal style.

Characterized by her enviable long mane, Pippa Middleton made the shock decision to go for the chop in 2014. That fall, she supported her brother-in-law, Prince Harry, at the Invictus Games and showcased her new lob cut, which is essentially a longer bob. Wearing her recently trimmed tresses down, she sported soft curls, which gave her an old-school Hollywood glam look. Although a deviation from her usual looks, the shorter style looked chic and sophisticated on the socialite.

The lob was the most popular hairstyle of 2013, seen on stars such as Jennifer Lawrence, Demi Lovato, and Nicole Richie. Middleton was fashionably late to catch the wave of the lob's popularity, and by 2014 there was already a fierce backlash against the divisive style, with rallying cries for it to die off. Then again, Beyoncé was also late to the lob game, joining Pippa in debuting the style in 2014. If it's good enough for Queen Bey, it's good enough for the Princess of Wales' little sis.

Who's that girl? It's not Jess, aka Zooey Deschanel, it's Pippa Middleton. The socialite made a surprising style statement while attending a gala for the British Heart Foundation in 2015. Channeling Deschanel's signature hairstyle and retro-tinged red carpet fashion, Pippa was a dead ringer for the twee icon. Wearing her hair in cutesy, glossy ringlets, she even pinned one side of her locks back with a dainty hair clip, which almost resembled scene kid side-bangs (trust us, "scene kid" and "Pippa Middleton" are not words we expected to use in the same sentence).

It was a notable departure for Pippa, who typically favors mature hairstyles over anything overtly girly. But the kitsch look suited her, and the twee aesthetic was, of course, very much in vogue for the 2010s. All that was missing was a Peter Pan collar and some mustard-colored tights, and Pippa could have easily fronted her own adorkable "New Girl"-esque sitcom.

2016 was a big year for Pippa Middleton. She announced her engagement to James Matthews, a wealthy hedge fund manager and former racing driver. Unfortunately but somewhat inevitably, the news led to cruel comparisons between the Middleton sisters, with the Daily Mail inexplicably claiming that Pippa had somehow outdone Princess Catherine by bagging a multimillionaire beau. However, Catherine didn't heed this toxic discourse, and was reportedly overjoyed for her sister.

The engagement wasn't the only major change in the younger Middleton sister's life that year. She also changed up her hairstyle, which had grown quite a bit since her aforementioned lob. Sitting in the stands at Wimbledon, she looked effortlessly cool as she donned shades and pin-straight, sleek hair. Indeed, Pippa was serving supermodel, channeling the catwalk icons of the '90s and early 2000s. While chestnut waves are her signature style, the ironed mane suited Pippa Middleton's angular features and retro-inspired dress.

A testament to her popularity among the British public, Pippa Middleton and James Matthews' wedding was a momentous occasion that attracted hordes of royal fans and onlookers. The 2017 ceremony took place in the quaint village of Englefield and was attended by royals and celebrity guests alike.

Prior to the ceremony, there was speculation as to how Pippa would style her hair. "It won't be anything outrageous, but my money would be on a textured up-do as she is rarely seen with her hair up and it would make more of a statement," hairstylist Jordan Garrett told The Telegraph. And, as it turns out, Garrett was right on the money.

On the big day, Pippa did not disappoint with her bridal look; her classic lace gown was accompanied by a chic updo that featured a Dutch braid delicately coiled around her head. Wearing a diamond barrette that resembled a small tiara, she looked like a princess in her own right as she walked down the aisle. Pol Garcia was the talented stylist behind her majestic hair. "What an experience," Garcia wrote on X (via Express), "thank you Pippa for trusting me with your hair on your special day."

Pippa Middleton has had her share of controversial moments, but no one was quite prepared for the dramatic hair statement she would make in 2017. Although she had grown her locks more or less to her signature length from before her 2014 cut, Pippa once again reached for the scissors in the fall of 2017, debuting a blunt bob. She continued with the style into 2018, and that January, she was snapped heading to church with a slightly asymmetrical, pin-straight bob.

Unlike her previous lob, this hairdo was shorter, straighter, and more dramatic. Pippa was praised for the haircut, with The Telegraph declaring it her chicest style yet. It was also a highly versatile cut, a plus for someone like Middleton, who's keen on frequently experimenting with different 'dos. "It's broadly complimentary with a balanced length that doesn't stifle styling versatility," hair stylist Kristan Serafino told Allure. "A blunt lob cut will simply transition between beachy waves to super stylish with little effort."

After making her mark on the royal landscape at her sister's 2011 nuptials, Pippa Middleton wasn't done wowing the crowds at royal weddings. In May 2018, she attended Prince Harry and Meghan Markle's highly publicized wedding at Windsor Castle. If one was expecting Middleton to re-hash her previous matrimonial looks, though, they'd be mistaken.

She opted for something totally new, donning a simple bun accessorized with a blush pink fascinator. The hairdo perfectly complemented the simplicity of her dress, with Pippa wearing a silk floral number dubbed the "Hepburn," a rather fitting moniker considering that her hair harked back to classic updos of Audrey Hepburn. Moreover, the fascinator made an interesting change for Middleton, who typically isn't known for hiding her locks under headgear. Accordingly, the flawless look was more old-money aristocrat than party girl, establishing Pippa Middleton's status as a royal-adjacent style icon.

According to the book "Finding Freedom: Harry and Meghan and the Making of a Modern Royal Family," Pippa was worried that Meghan would overshadow her at her own wedding the previous year. It therefore makes sense that she opted to remain markedly low-key for Harry and Meghan's nuptials, ensuring that she didn't draw attention away from the bride.

By the summer of 2018, a pregnant Pippa Middleton was embracing maternity chic. Attending Wimbledon, she wore a floaty floral dress and an equally simple hairdo. Or so it would seem. At first glance, it may have appeared that Middleton was sporting a basic ponytail. However, she is nothing if not full of surprises. Pippa actually had a sneaky braid woven into her hair, which recalled her iconic bridal look the previous year.

The trendy hairstyle was an extension of Middleton's belief in self-care during pregnancy, a time that is, for many pregnant people, a stressful experience. It was also a nod to her love of tennis, with the sporty style a staple of players at Wimbledon. Chatting to Waitrose that year, she revealed that she was still playing tennis while pregnant. "If you're a seasoned player and take care, it's possible to play right up until the third trimester," she said.

Over the years, Pippa Middleton has slowly been carving out a niche for herself with her braided hairstyles. In 2019, she attended a charity gala for the British Heart Foundation, where she rocked a stylish updo and milkmaid braids. It was an unusually boho look for Pippa, who complemented her hairstyle with a long '70s-style printed dress. Once again, she proved that she's unafraid of experimenting with different coiffures and stepping out of her comfort zone.

It was a chic hairdo, but it's not the easiest style to fashion out of Middleton's famously silky mane. Speaking to Hello!, hair stylist Patrick Wilson explained that folks need to wait until a day or two after they've washed their hair in order to achieve the desired results. "This style works best on next day hair," Wilson explained. "I would add a dry shampoo for extra texture." Middleton had clearly been heeding such advice, with the usually pristinely presented star rocking a few noticeable flyaways.

In 2021, Pippa Middleton returned to her signature silky chestnut locks. Attending a Christmas service at Westminster Abbey, her hair was impossibly glossy and bouncy, partly pinned back with strands framing her face. Embracing her dark hair and eschewing dramatic dye jobs, Pippa has become something of a natural beauty icon.

Accordingly, her love of the natural look has in turn encouraged other women to ditch the dye and embrace simplicity over trends. "When Pippa Middleton appeared in the public eye during the 2000's she definitely inspired many women with her natural beauty, flawless skin and soft beautiful waves," hair stylist Jessica Patching told Express. "Seeing Pippa with not overly styled hair making the appearance seen as simple and organic influenced many women to embrace the more natural way." Patching added that Middleton had helped normalize the notion that women needn't be constantly changing up their coiffures or regularly dying their hair in accordance with trends.

Queen Elizabeth II's platinum jubilee celebrations in London were as spectacular as they were poignant. The jubilee weekend, which took place in June 2022, marked Her Majesty's final public appearance before her death just three months later. Showing solidarity with the royals, Pippa Middleton took part in festivities and donned a bright emerald green dress; it was a subtle yet fitting tribute, perhaps, to the ailing queen, who was famed for her love of bright colors and wore the same bold shade when she graced the Buckingham Palace balcony one last time. 

To complement her vibrant dress, Middleton embraced playful twisted beach waves. This time, her hair also featured some lighter highlights, which accentuated her bouncy curls and contrasted perfectly against her statement dress. The fairer hair was a major departure for Pippa, but fans were loving it. "She looks so good with this hairstyle," one royal fan commented on Instagram (via Express), while others praised Middleton for her understated approach to style.

Royal fans can't help noticing that Princess Catherine and Pippa Middleton have very similar style, and these similarities extend to the sisters' approach to hair styling. In December 2023, Pippa appeared at a festive charity gala for the British Heart Foundation, and, at first glance, one would be forgiven for mistaking her for her older sister. Replacing the luminous highlights of the previous year with her quintessential chestnut hues, Pippa wore her hair in gentle cascading waves, the likes of which are frequently donned by her sister. Channeling Catherine even further, she was also wearing a dress by Self-Portrait, which is one of the Princess of Wales' favorite brands.

Although Pippa Middleton suits just about any 'do and has undergone a stunning hair transformation throughout the years, the bouncy brunette waves were a welcome return. Indeed, the star is a natural beauty icon, forever serving as inspo for embracing what one already has.