Kate Middleton's Most Iconic Pre-Royal Fashion Moments

Oh, to have the closet of Catherine, Princess of Wales. She always steps out looking stylish from head to toe no matter where she's headed, whether it's an engagement with one of her patronages or the royal family's annual Christmas walk to church. Kate Middleton has even taken some bold fashion risks that definitely paid off.

Long before her days as a princess, Kate's fashion may have made a big impact. Before she began dating William, Prince of Wales, they were friends at St. Andrews University. He saw her wearing a sheer Charlotte Todd dress at a charity fashion show and was reportedly mesmerized. Classmate and friend Ben Duncan told E! News in a 2011 interview, "He was sitting front row and his eyes were like stalks." Duncan felt Kate's modeling was a game-changing moment for her and William's relationship, although they reportedly didn't start dating immediately after, remaining friends for a while.

Even off the runway, pre-royal Kate was rocking some iconic looks.

While Catherine, Princess of Wales was still dating William, Prince of Wales, one of the many places she showed off her fashion sense was at sporting events. In June 2006, she wore a red halter dress with small white dots to a charity polo match called the Chakravarty Cup. It was belted with a wrap-around tie around her waist. Kate Middleton kept her long brown hair down and matched the dress with a pair of sunglasses and simple silver jewelry. 

The outfit was an ultra-fashionable WAG look since Kate was there to watch William playing in the polo match. The dress also almost feels like foreshadowing, since polka dots became a staple for Kate's wardrobe into her royal years. Dots are also one of the ways Kate has channeled the late Princess Diana's iconic style. However, the dots on her Chakravarty Cup dress were a lot smaller than the bigger, more noticeable dots on many of Kate's future fashions. 

Another of Catherine, Princess of Wales' most iconic pre-royal fashion moments was her ravishing red look from William, Prince of Wales' Royal Military Academy graduation. Kate Middleton was photographed at the December 2006 Sovereign's Parade wearing a bright red overcoat. She paired it with a black blouse or dress with a lace neckline, black tights, and black boots. Her gloves, clutch, and hat were also black. In the above photo, Kate smiled alongside her parents, looking like a bright beacon amongst their darker clothes.

Kate's Philip Treacy hat from the 2006 Sovereign's Parade was adorned with a big bow. It was brought out again and worn on multiple occasions by the royal following her marriage to William, namely at Remembrance Sunday events from 2012, 2017, and 2023. That fabulous hat was just one of the times Kate repeated a gorgeous royal look.

Catherine, Princess of Wales and William, Prince of Wales' 2007 split may have been because of Queen Camilla's interference. However, no matter the truth of what really drove them apart, the breakup didn't last long. During their time apart, Kate Middleton didn't wallow at home. She stepped out in a stylish and preppy outfit for the Badminton Horse Trials in May 2007.

Kate paired a white denim skirt with a navy sweater and collared shirt. She accessorized with suede boots, a thick belt, sunglasses, simple jewelry, and a slouchy purse. The outfit was very posh, but it didn't feel stuffy or impossible to put together oneself — which Vogue writer José Criales-Unzueta pointed out while being interviewed for a piece they published on Kate's fashion sense in the 2000s.

Criales-Unzueta also mentioned some of Kate's favorite fashion pieces (including suede boots) and added, "This princess wasn't a 'glamazon' or a supermodel in runway samples. She was the girl next door and dressed the part — which means that all those eyes watching her didn't feel challenged by her style. Instead, they felt seen by the normalcy of her clothes."

Catherine, Princess of Wales' brief independence as a single woman in 2007 included her and her sister Pippa Middleton enjoying time out together. In the above snapshot from that time, Kate Middleton smiled brightly while wearing a handkerchief maxi dress. The shiny, silky dress was gray, white, and gold, and the fabric was printed with florals and other regal-looking flourishes. It also had playful spaghetti straps and a V-neck.

The look was reportedly for a visit to the Mahiki Mayfair bar. Kate's dress contrasted well with Pippa's all-black look, and both sisters looked fashion-forward and ready for fun. It seems like the Mayfair location of Mahiki is closed as of writing, so Kate and Pippa would have to choose another location if they wanted to return for a trip down memory lane. 

The iconic handkerchief dress is also an unlikely fashion piece for Kate to re-wear now, as a royal and mother of three. However, at a posh wedding a few years later, Kate wore a silky dress with a refined twist.

Catherine, Princess of Wales was a guest at the wedding of Nicholas van Cutsem and Alice van Cutsem (then Alice Hadden-Patton) in 2009. William, Prince of Wales and Prince Harry were good friends with Nicholas growing up due to their fathers being friends, so William was an usher for the festivities.

Kate Middleton's ensemble included a silver satin knee-length dress under a blue overcoat, and the blue was a very flattering color on Kate. Her coat (from designer Jane Troughton) and dress both featured brocade-like pattern in the fabrics, although it was classy and understated. The belt of the coat was also embroidered with flower shapes. Of course, it wouldn't be a wedding for the royal-adjacent without fascinators, and Kate's for the wedding was the same colors as her outfit.

This was one of Kate's pre-royal fashion moments that likely solidified her status as one of the royal family's most influential fashion icons. For more, check out how Kate's style has evolved over time.