When it comes to street style stars, few individuals have garnered as much attention as Alexa Chung. The English It girl created the blueprint for today’s social media influencers, parlaying a permanent seat in the fashion front row to brand collaborations and eventually her own label. But Chung’s path to success actually began in the modeling world, where she got an early start appearing in teen magazines before landing a gig as the co-host of the British television program Popworld in 2006. Within five years, Chung’s fashion savvy would make her a global sensation, bringing with it a list of milestone achievements that included an eponymous Mulberry handbag, a Madewell collaboration and a British Vogue cover—all in just three months.

“It’s all about effortlessness. It’s all about looking underdone,” Chung said in a 2010 interview with the New York Times when discussing her signature beauty look of tousled hair and various stages of overgrown fringe. That effortless approach has always applied to her sartorial choices as well, where Chung is as likely to turn to rock stars like Mick Jagger and George Harrison for inspiration as she is to female style icons like Jane Birkin or Kate Moss (though she’s certainly looked to both of them, too). “As much as I love denim and men’s tailoring, I also have this weird affection for very girly, saccharine gowns and dresses,” Chung has said of her styling choices, which often blend masculine and feminine pieces in unexpected ways.

While Chung’s red carpet looks often embraced those girlish elements with the detailed gowns expected of more formal events, her off-duty moments have always served as a perfect way to showcase the amalgamation of her style references. With a wardrobe packed full of vintage finds, casual denim and coveted designer pieces, Chung’s effortlessly cool street style looks always had a touch of accessibility to them, too—something that no doubt helped her to become a style icon in her own right.

Whether you’re looking for a bit of style inspiration or feeling nostalgic for early 2000s fashion, take a look back at some of Chung’s most memorable off-duty fashion moments.

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When she wasn’t being photographed outside of fashion shows, Chung brought her street style stardom to Glastonbury Festival, where she traded her usual ballet flats for more practical Wellies.

The official launch of Mulberry’s Alexa handbag (named after and inspired by Chung, of course) was still be a few months away, but as the British brand’s muse, Chung got to debut the bag a little early during New York Fashion Week. The it bag of the aughts, Mulberry would go on to relaunch the bag more than a decade later as part of its 50th anniversary celebrations.

Trench coats featured prominently in Chung’s wardrobe over the years, but until she started designing her own (both with her namesake label and as collaborations with other brands), a classic Burberry trench was her go-to. For the fashion house’s spring 2010 show (she also served as the afterparty’s DJ), Chung paired her trench with another classic: a little black dress, which she accessorized with a........

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