Princess Kate's Cheltenham Festival outfits turn heads every year for their quintessential style; however, the ensemble she wore almost two decades ago takes the top prize for being her coolest yet.
The 44-year-old senior royal, who was 25 at the time, attended the fourth day of the horse racing festival in Prestbury, Gloucestershire, in 2007 without Prince William. She joined friends in the royal box, taking in the action below with a pair of binoculars.
At the time, Kate was dating the young prince, but their relationship hit a rocky patch right after her day out at the races, following which they announced their breakup in April of that year.
From her perch, she radiated "cool It-girl" in an outfit that screamed Parisian chic, featuring a brown beret.
The mother-of-three sported a look by London-based designer Katherine Hooker, wearing a duck-egg blue woollen blazer with brown buttons running along its seams. She added a chocolate-brown midi-skirt and allowed her jacket to be the centre-piece of the ensemble.
Kate added a white shirt as her base layer and accessorised with a paisley-patterned scarf in earthy greens, reds and blues to match her blazer.
On her feet, she walked around the race course in knee-high suede brown boots that featured a chic skinny heel and carried her belongings in a medium-sized leather brown bag slung over her shoulder.
© UK Press via Getty ImagesShe jazzed up her muted tones with a pair of dangling silver chandelier earrings partially hidden under her long chestnut hair, which she wore loose around her shoulders.
Completing her beauty look, she kept her makeup extremely neutral, including a barely-there nude lipstick and a subtle touch of eyeliner.
Showing off her style, Kate spent the day watching the course from above with some friends and was spotted giggling and recoiling in shock as she joined in with the equestrian fun.
© UK Press via Getty ImagesA make-or-break year for the budding princess
Aside from her outfit choices, 2007 was a big year for Kate as it was a pivotal turning point in her romantic life.
By then, she had been dating Prince William since 2002, following their initial meeting at the University of St Andrews, where they were students on the same course and living in St Salvator's Hall.
Nearing the five-year mark, the couple revealed they were going their separate ways in April 2007, and it was reported at the time that the breakup happened over the phone.
© POOL/AFP via Getty ImagesIn his biography, William and Catherine: The Intimate Inside Story, Russell Myers revealed: "Catherine delivered an ultimatum to William. While she did not explicitly demand an engagement or even a promise of marriage, she did break free from the gentle and arguably submissive persona that had typified her relationship with the future king."
Short-lived, they reconciled later on that same year and continued dating until William proposed to Kate on October 20, 2010.
They walked down the aisle at Westminster Abbey in London one year later, in 2011, and went on to welcome three children together: Prince George, 12, Princess Charlotte, ten, and Prince Louis, seven.
