Growing up, there was no one that I was more obsessed with than Sofia Coppola. The New York-born daughter of Hollywood legends Francis Ford and Eleanor Coppola had directed some of my favorite films as a teenager: The Virgin Suicides, Lost in Translation, Marie Antoinette, Somewhere. She was also the reason I aspired to be a director, and actually thought it was possible as a woman, in a world before Kathryn Bigelow became the first woman to win the best-director Oscar.

But there was also the matter of her style. Here was an It-girl who shrugged off that mantle—one with a penchant for laidback, understated looks, who also always had a certain polish and never-less-than-impeccable taste. Through the ’90s, she lived in silk slip dresses, turning up to glitzy LA premieres in flats and running back to New York as soon as she could to stroll the city in denim and cashmere. There was an ease to her ensembles, a kind of careless intellectualism, but also a very precise understanding of and appreciation for fashion.

This comparatively carefree heyday is about to be revisited in Marc by Sofia, the auteur’s first-ever documentary, which will chronicle the rise of her longtime friend and collaborator Marc Jacobs. Billed as both a highly personal love letter and an ode to ’90s New York, it’s sure to be crammed with swoon-worthy fashion moments, courtesy of the pair and their glittering circle of friends.

Ahead of its premiere at the Venice Film Festival, we revisit 36 of the best throwback photos of Sofia, tracking her evolution from industry scion to stylish young actor, model, and designer, and eventually, one of the most accomplished filmmakers of her generation.