The Stunning Style Transformation Of Pippa Middleton

Even though the first thing that comes to mind when you envision Pippa Middleton might be the white, fitted bridesmaid dress she wore to her sister Kate Middleton's wedding, she's had her share of stunning style moments all her own. As a socialite, author, and mom of three, Pippa is busy — and often in the public eye. This means there's plenty of pressure to look polished at all times, and she typically pulls this off. From playful prints in her early years at prestigious parties and balls to sophisticated maternity wear and sporty but chic swimsuits, Pippa has proven she knows how to style herself elegantly, no matter the situation.


Although she loves sports and staying active, Pippa has no problem looking ultra-feminine in flowing dresses or classic silhouettes. She's probably also not someone you'd ever see in spring 2024's most divisive fashion trends. Not only does she have a flair for dressing both chicly and practically but she's also shown off some pretty amazing maternity styles, proving that maternity fashion can be just as exciting and stylish as non-maternity fashion. Although Pippa's style may not have undergone any wild or drastic changes over the years, it has subtly evolved into something both playful and sophisticated that truly turns heads.

2007-2009: She's all about playful print dresses

In 2007, 24-year-old Pippa Middleton was a fixture at events and parties, like the book launch of Simon Sebag Montifoire's "The Young Stalin," which she attended with her equally well-dressed sister, Kate Middleton. She wore a silky, textured gold dress with a black, floral motif, which she paired with a cropped, black cardigan and black, sling-back pumps.


Throughout this period, Pippa could be seen dressed beautifully at plenty of parties, galas, and balls. Knee-length dresses with circle skirts were common picks for her, as were cropped cardigans. Waist-accentuating wrap dresses with floral details were big style staples, as were ones with lace.

She often pulled together outfits with simple pumps or wedges, and her other accessories were also simple but still glamorous, like gold jewelry and a dainty gold wristwatch that she wore with multiple outfits. For more formal occasions, her dresses were floor-length but still simple, featuring large, floral patterns and minimal gem detailing. She also kept her hair and makeup low-key, proving that a little eyeliner and blush can go a long way toward cultivating a polished look.


2010: Glitz, cutouts, and cute skating style

By 2010, Pippa Middleton grew more adventurous with some of her looks and departed slightly from some of the styles she'd relied on previously. At The Reuben Foundation & Virgin Unite Haiti Fundraiser, Pippa rocked a short, gem-encrusted frock with a large chest cutout. She paired this gray, eye-catching dress with pantyhose, black pumps, and a black clutch. Her layered hair and makeup looked naturally polished as usual, which only drew more attention to her intriguing and flirty dress.


Also in 2010, Pippa showed off her cute skating style at the Somerset House in London at an event presented by Tiffany & Co. In a belted coat with large buttons and lapels that showed off her shape, she hit the ice and had some fun. Fitted black pants, gold jewelry, a furry brown scarf, and, of course, some skates completed her casually chic look.

2011: Pippa snags attention in an iconic bridesmaid look

While many in the United Kingdom were already familiar with Pippa Middleton, everyone officially met the 27-year-old socialite when she served as a bridesmaid at Kate Middleton's wedding. In the televised event, Pippa appeared in a figure-hugging white dress designed by Alexander McQueen creative director Sarah Burton. This look became instantly iconic and even marked a turning point in how we view wearing white in the last 100 years of bridesmaid dress styles, much to Pippa's surprise. In a conversation with Today, she touched on the dress's popularity, saying, "It was completely unexpected. 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."


Of course, her bridesmaid dress wasn't her only significant look that year. As the paparazzi took more photos of her — likely because of her appearance at Kate and Prince William's wedding, aka her entrance into the royal spotlight — we got an even better look at her evolving style. This was a year of comfortable but cute flats, structured blazers in black, navy, and cobalt blue, and breezy blouses. Jeans, sunglasses, and above-the-knee dresses played big parts of her casual looks, while floral motifs, fascinators, and pumps remained staples of her more formal looks.

2012: Classic jackets and bright pops of color define Pippa's style

By 2012, Pippa Middleton was taking her style in a new direction and introducing more color. Her street style still featured plenty of dark, structured blazers and light blouses with frilly details, but she began pairing them with bold, red jeans and bright, red cropped pants. Sunglasses and large bags were typical accessories for her, too. When it came to her hair, high ponytails were a frequent pairing for her casual looks.


Pippa could be seen on the sidelines at Wimbledon this year as well, looking polished as ever. Classic Channel-style jackets make more than one appearance, which she couples with delicate gold jewelry and dark skirts. At the U.S. Open, she rocked a bold but summery color-blocked dress featuring orange, green, and navy blue. In more formal settings, like parties and book launches, Pippa often wore two-tone dresses. At the launch of her book, "Celebrate: A Year of Festivities for Families and Friends," which is full of hosting tips and recipes, she slightly departed from her more colorful looks and wore a simple but fitted burgundy dress.

2013: Pippa dons playful patterns, sequins, and feathers

In 2013, 30-year-old Pippa Middleton continued amping up the fun in her outfits. She kept up the theme of bold colors, like when she wore a canary-yellow peacoat paired with a fur hat, dark tights, and dark boots to the Cheltenham Festival or the mint-green knit dress and button-up cardigan she donned to the Aegon Championships at Queens. However, she now began playing with her style in new ways.


Exotic-looking floral motifs and patterns still appeared frequently in Pippa's looks, as did the occasional lace dress, but this year, she branched out to new textures, like feathers and sequins. At a donor dinner in London, Pippa wore a flapper-esque blue dress featuring dark blue and bright peach feather details along with shiny beading. At the Sugarplum Ball, she paired her elegant and intriguing black lace dress with a black sequin top. A sleek updo and some dangling earrings pulled it all together.

2014-2015: Coat dresses and bold, bright hues make a put-together Pippa

By now, Pippa Middleton had solidly established her style, which was often defined by bright colors, floral prints, and classic silhouettes. During 2014 and 2015, she seemed to get even more comfortable with these elements and truly knew how to style them to look her best. In early 2014, coat dresses were go-tos for 31-year-old Pippa. At Arabella Musgrave and George Galliers-Pratt's February 8 wedding, she donned a nude-toned one paired with a nude fascinator and black pumps. Later, at Sir David Frost's memorial service on March 13, she wore a black one accessorized with gold jewelry and a black clutch.


Later that year, Pippa wore another nude dress to the GQ Men of the Year awards event, this time a subtly glitzy one with sheer layers and sequins. When she wasn't keeping it toned down with neutrals, Pippa really shone in bold and bright colors, like the two-tone hot pink and purple dress she wore to the wedding of Anneke von Trotha Taylor and Charlie Gilkes, which made for the perfect semi-formal wedding dressing, or the swishy blue mullet dress that featured flower-shaped gem detailing that she wore to the Boodles Boxing Ball.

2016: Pippa's style features tructured simplicity

Around 2016, Pippa Middleton's looks began to veer away from bold pops of color. Many of her styles took on a new and refreshing simplicity and tend to be structured. Her white dress with black accenting paired with red pumps that she wore to the British Heart Foundation's Roll Out the Red Ball is a great example of this. The gray dress with the long pleated skirt she wore to the Disability Snowsport UK ParaSnowBall also highlights this style shift, as does the elegant gray jumpsuit she donned for BGC Annual Global Charity Day. Despite going for more subdued looks at her formal appearances, she still showed off her fun sense of style at more relaxed events, like Wimbledon, where she was seen in breezy floral and geometric-patterned dresses.


This was also the year Pippa announced her engagement to her hedge fund manager boyfriend, James Matthews. While talking to the Daily Mail, she spoke about how her opinions on wedding attire have changed over the years. When Daily Mail asked if she'd wear tennis shoes to her wedding, as she claimed she would as a child, she said, "No. That was a phase I went through as a little girl and I was having a bit of a battle about wearing a dress. I wasn't into dresses as an eight-year-old."

2017: Pippa has fun with lace, frills, and a wedding gown

At 34, Pippa Middleton made waves in white once again, but as a bride this time. She married James Matthews at St. Marks Church and was absolutely glowing. Her wedding dress was a simple cap-sleeved lace gown with a train, which she paired with a sheer veil and delicate tiara. The dress was dreamed up by British fashion designer Giles Deacon, who spoke to Business of Fashion about the dress' creation, saying, "I wanted that 'how-was-that-done?' factor. It's all hand-pieced which is why you actually don't see a seam." He also acknowledged Pippa's involvement in the design, adding, "She has a great eye, she knew what she wanted."


Her wedding dress might have been a specially tailored creation, but that doesn't mean that Pippa wasn't rocking plenty of other amazing looks that year. At the Miles Frost Fund party, she wore a chic, white jumpsuit paired with red accessories. Then, at Wimbledon, she wore a pastel dress made with multiple kinds of intricate lace, which she accessorized with a gray clutch and sunglasses.

2018: Breezy maternity style enters the scene

In 2018, Pippa Middleton's growing baby bump was on full display, which meant she got to show off her maternity style. In many ways, her fashion choices were similar to those she made pre-pregnancy, although the specific cuts and shapes of her dresses were more accommodating for her growing bump. At Meghan Markle and Prince Henry's wedding, she wore a charming, green and pink floral print dress with large pleats where her bump was just becoming visible. She paired it with a nude fascinator and strappy nude pumps.


At the French Open that year, Pippa donned a breezy, red-and-white nautical-themed print dress, which she paired with sunglasses and a fedora. Later that year at Wimbledon, she accessorized the same way, this time wearing a fedora with blue pompom accents. At her nephew Prince Louis' christening, she was seen in a simple and chic powder-blue dress with a dropped waist, and a few days later, she was seen in another drop-waist dress, once again at Wimbledon.

2019: Pippa looks adorable in flowy florals

At 36, Pippa Middleton left maternity wear behind and was back to donning waist-accentuating dresses. As always, florals made up a big part of her overall style. At Wimbledon, she wore a long, pink floral print dress that truly popped, along with simple accessories, like white sandals and a white clutch.


While stickig to florals, Pippa still played around with her style in other ways. For example, new shapes and structures began to show up. At Lady Gabriella Windsor and Thomas Kingston's wedding, Pippa wore a blue eyelet dress with buttons running from the collar all the way down the dress. It also featured bold, layered puff sleeves. Pippa accessorized it with a large, blue velvet headband, which shows she was branching out with her accessories, too. At the Beating Hearts Ball in support of the British Heart Foundation, she wore another intriguing dress with large ruffles at the shoulders, which featured an eye-catching red and white geometric pattern.

2020-2021: Pippa looks polished and relaxed in blues and casual neutrals

By 2020, Pippa Middleton's street style was soft, neutral-toned, and the epitome of the rich mom aesthetic, an even more sophisticated evolution of the quiet luxury trend. Throughout this period, paparazzi snapped her wearing long neutral-toned coats, gray trousers, jeans, breezy blouses, and comfortable-looking sneakers.


She also got candid about pregnancy and fitness for the shoe brand Hoka, writing on the brand's blog, "Being active with my two-and-a-half-year-old son in the park or playground, transporting him on the back of my bike, and buggy running when he was a baby have been ways in which I have been able to include outdoor exercise whilst being a hands-on mummy." It came with benefits, too, with Pippa adding, "It's helped manage my weight, is time efficient, and gives us both the chance to enjoy the fresh air and explore the great outdoors."

Her comfortable and practical but still incredibly polished outfits from this time were a departure from her bright-colored dresses and heels, but these changing fashion choices seemed to highlight the changes in Pippa's life — and her need to keep up with her active toddler.


2022: Pippa rocks bold maternity dresses and long coats

In 2022, 39-year-old Pippa Middleton showed off her effortless and adorable maternity style again. Comfortable but charming dresses were popular choices for her. At a Jubilee concert, she wore a bold, kelly-green dress that made her look totally radiant. It featured a notch neck and a smocked chest and sleeves, with delicate silver jewelry and impeccably curled hair bringing everything together.


Pippa could be seen in another flowy-looking dress while taking her son for a walk. This time, it was a navy blue flower-print dress with a ruffled V-neck. She paired the dress with blue sneakers and minimal jewelry. Also that year, Pippa was pictured in London wearing another breezy, comfortable, and incredibly cute flower-print dress, which she paired with sneakers, rounded sunglasses, and a messy bun. Once again, Pippa proved that maternity style is anything but frumpy by putting together charming styles without sacrificing comfort.

2023-Present: Pippa showcases classy beach style and rocks pastels and fascinators

Being athletic and outdoorsy, 40-year-old Pippa Middleton knows how to dress for the beach. While Pippa has showcased her great swimsuit style many times, she really showed it off in 2023. Now a mom of three, Pippa has proven she still knows how to rock a swimsuit. Often in simple but trendy bikinis, she shows that she's just as good at looking polished and put-together at the beach as at a wedding or walking around town.


While on vacation in Italy, Pippa was pictured going for a dip in a feminine, pastel peach and green bikini. On the same vacation, she was pictured in another feminine but classy bikini, this time a bubblegum pink one with a deep V accent on the top. Earlier in 2024, Pippa hit the beach in St. Bart's in a trendy white Stella McCartney tennis dress, which she paired with sunglasses and a straw tote. Also on this vacation, Pippa wore a bikini in one of her signature colors, bold green, with gold accents.

Of course, Pippa still has formal events to attend and looked elegant at King Charles III's coronation, where she donned pale yellow, the ultimate no-color color. Her butter-yellow coat dress was simple and refined, especially with its matching fascinator. Ultimately, with all these years of fashion under her belt, she'll likely never land on our list of celebs with the worst style — but it's still a great list to read.