Caitlyn Jenner

Kim Kardashian might have sought to break the internet with her cover of Paper magazine in 2014, but it was her step-parent Caitlyn Jenner that starred on the most memorable cover of the year. When the former decathlete and Olympic gold medalist, born Bruce Jenner, announced her transition in Vanity Fair, an activist and a fashion icon was born.

For the elegant Annie Leibovitz shoot, Jessica Diehl styled Jenner in soft yet sensual looks, pulled from Zac Posen and Donna Karen to name a few. Following the release of the cover, the designers and brands that hadn’t already dressed her clamoured to do so. The emerging fashion plate’s dress for the ESPY awards, in which she was honoured with a bravery award, was a floor length custom made white Aetelier Versace gown. Donna Versace herself contacted Jenner to offer to dress her. Since her acceptance speech from the awards went viral, Jenner’s sartorial choices have been closely studied by the industry. She has since worn Diane Von Furstenberg and Tom Ford , and held meetings with Patricia Field.

In March 2016, a 66-year-old Jenner was announced as the face of H&M Sport. Later that year, H&M created a six-minute film featuring Jenner, called "Caitlyn Jenner's Greatest Victories: A Timeline." From 2015 to 2016, Jenner starred in the reality television series "I Am Cait," which focused on her gender transition and, in January 2017, she underwent sex reassignment surgery. Jenner has been called the most famous openly transgender woman in the world.

While her online influence and status in popular culture no doubt appeals to brands and designers from a marketing point of view, Jenner’s fairytale transformation also fits with fashion’s central narrative — she is a model to show how you can truly express your identity through clothes.