Kate Moss rose to prominence at a time when Britpop was at its peak, becoming a poster girl for the glamorous grunge associated with the decade in her ultra-minis, oversized fur coats that almost swallowed her whole and penchant for hanging out of windows smoking cigarettes.

As a result, the London native has become fashion’s equivalent of a rockstar: full-throttle hedonism, late nights, long parties, black leather and pure rebellion. “I would have wanted to be a lead singer, if I wasn’t a model,” Moss once said, almost apocryphally. “I’d go touring in a bus with my band. In my next life, that’s the plan.”

Dissecting her most iconic fashion moments through this framework helps to understand the sartorial choices she makes, like bringing two Hermès bags to the beach in Formentera, wearing a nearly-naked slip dress to an Elite Model party or trotting through Notting Hill in Vivienne Westwood pirate boots and a Napoleon jacket. Even to this day, Moss is not one to follow rules, nor trends for that matter. Still, she can’t seem to help the fact that she often sets them, with her sleaze-infused dress sense an aspiration for many.

This is especially true as autumn approaches. As the seasons change and the weather shifts gears down into something more morose and crisp, Moss’s ability to layer dark hues, inject texture and style slouchy staples becomes the pinnacle of off-duty chic. The latter point is especially relevant given she does it all without sacrificing her own personality, with every large jacket and skinny jean outfit a reminder that elevated basics do not have to be synonymous with the term boring.