Catherine Middleton, now adored as the Princess of Wales, wasn’t always destined for royalty, unlike her husband, Prince William. However, beyond her royal title, Catherine has made a significant impact with her dedication to philanthropy and continues to be the epitome of elegance. While her sister, Pippa Middleton, first rose to fame with the iconic dress she wore to her sister's wedding to Prince William, Pippa’s style tends to lean toward more conservative choices. Yet, there have been times when Pippa, much like Catherine, has made bold fashion statements that are, by royal standards, quite daring.
We're all familiar with the stunning looks both sisters sport at high-profile events, from Wimbledon to the annual Royal Family carol concert. But there’s more to them than just glamorous gowns and royal appearances. In a rare, unearthed photo from 2006, the Princess of Wales, then Catherine Middleton, stunned in a teal dress at the Boodles Boxing Ball at the Royal Lancaster Hotel in London. The dress featured a silky ribbon belt, and she wore her hair in soft waves. Another image from February 2007, shows a 25-year-old Catherine, alongside her 23-year-old sister Pippa, heading to the popular London hotspot, Mahiki. Catherine wore a silver and yellow satin midi dress with spaghetti straps, a plunging neckline, and a floaty skirt, her signature bouncy blow-dry making an appearance.
Pippa Middleton, while dazzling in her bridesmaid’s dress by Sarah Burton at her sister's wedding, also wowed at the evening reception. She wore an emerald green floor-length gown adorned with Diamante detailing at the waist and shoulders. The dress, which featured a daring deep plunging neckline that showed off a hint of cleavage, was perfect for the event. Pippa’s bold fashion choice at the royal wedding was enough to almost overshadow Catherine's second dress of the day, which was a more traditional white.
But it wasn’t just at her sister’s wedding where Pippa turned heads. At the 2011 Boodles Boxing Ball, she donned a show-stopping fire engine red silk dress with a plunging neckline and a dramatic floral detail just beneath the bust. The look was daring yet sophisticated—a style more suited to a Cannes Film Festival red carpet than a royal charity event. While the dress might have been a little risqué by royal standards, Pippa, who was not a royal at the time, had the freedom to dress as she pleased. And she certainly did, turning heads in a look that was pure glamour for the star-studded event.
A candid photo taken at a polo match in 2009 shows the two sisters, Catherine and Pippa, enjoying a relaxed moment together. Both sisters were dressed in stylish yet casual outfits. Catherine, as always, looked impeccably put together in knee-high leather boots worn over skinny jeans, a floral top, and an oversized blazer. Pippa, meanwhile, had already begun to embrace a more royal-appropriate wardrobe, wearing a pair of cork wedge heels—often seen on her sister—and a smart navy dress. The two shared a moment of sisterly conversation with a glass of bubbles in hand, showing just how down-to-earth they can be.
These moments, from the sisters' casual style to their more daring fashion choices, highlight their effortless blend of royal elegance and personal flair. Both Catherine and Pippa prove that while they may be royalty, they are also relatable women with a strong sense of individuality and style.
