In 2003, Paris Hilton and Nicole Richie stood outside a clapboard barn somewhere in Kentucky (or somewhere that was made to look like Kentucky) with their hands wrapped around an iron rake. The late-teen heiresses spent five seasons of The Simple Life visiting agricultural families in the Deep South, where they repeated things like “Do you guys hang out at Walmart?” and “What’s a tax return?” to their bewildered hosts. Dressed in miniskirts and Louis Vuitton bikini tops, with Saddle bags dangling from the crooks of their arms, the duo managed to cultivate one of the most babe-tastic aesthetics of the ’00s. One which countless people are still trying to emulate some 20 years later.

“I was going for the Barbiecore vibes before there was even the word Barbiecore,” Paris Hilton explains in her Life In Looks video. “I invented it. Barbie is my idol, she’s such an icon. I’ve looked up to her my entire life and I always loved that Barbie could be anything she set her mind to. Whether it was a teacher or an astronaut or a president, this woman did it all.” The same could be said for Hilton, who, at 42 years of age, has lived numerous lives: as an influencer, a DJ, a fashion designer, a recording artist, an activist, an actress, a model, an NFT baron and a best-selling author. Here, she rolls back the tape on some of these former careers and the looks that have accompanied them.

There’s the spangled Julien Macdonald minidress she wore on 21st birthday in 2002, the pale-pink Kappa tracksuit she wore to a Golden Globes soirée in 2003, the Jackie O-inspired Self Portrait two piece she wore to the senate in 2023, and the Catherine Malandrino dress she wore to meet Karl Lagerfeld in 2006. “Love this legend,” she says. “He told me The Simple Life was his favourite show… he was definitely an inspiration for my gloves.” She paid homage to the late-designer once again at the 2023 Met Gala, where she attended as a guest of Marc Jacobs, dressed in sky-high Kiki boots. “I knew that it was going to be black and white, I just thought it was so chic,” she says. “Obsessed.”

So close is the bond that Hilton has forged with the fashion world, that when she tied the knot in 2021, 45 designers shipped bespoke wedding dresses to her Los Angeles compound. “My stylist was getting calls from designers all around the world and everyone was so excited to be a part of this wedding that they all made incredible custom dresses. So I tried to wear as many of them as possible,” she says, staring down at a photo of her Oscar de la Renta gown, which was just one of the six dresses that Hilton managed to wear on the night. “I wanted something that was really just like a princess, something that had, like, 3D flowers on it,” she adds. “I was going for a Grace Kelly vibe.”

From her “country sexy” looks in The Simple Life and her “sexy soldier” costume in “Stars Are Blind”, to her matching Louis Vuitton moment with Kim Kardashian and something she calls “DJ Barbie”, watch Paris Hilton’s Life In Looks for the backstories on some of her most iconic outfits of all time.