Billie Eilish’s affinity for oversize sweatshirts, rare high-end sneakers, monochromatic sets, and stacks of chainlink jewelry is an aspiration many people could only dream of pulling off. To an outsider, Eilish’s look can raise questions. Though she’s been on the receiving end of criticism, she’s well-aware that her out-of-the-box style is the ultimate combination of swag and relaxed comfort. The LA native is only 20 years old, but you can’t tell from her thoughtful, empowering lyrics and her range of vocal skills, or the 100+ million Instagram followers who keep up with her.

Eilish typically experiments with designs from household names such as Gucci, Oscar de la Renta, and Burberry, bringing depth to monochromatic outfits. Eilish is known for working with the designers themselves, from urging Oscar de la Renta to stop selling fur to becoming close friends with Gucci’s Alessandro Michele and serving as an active Gucci brand ambassador.

For Eilish, her style and clothing goes hand in hand with her relationship with her body, as she’s growing into a woman. In 2019, she told Elle magazine that the reason she opted to wear such baggy, oversized clothing was to prevent criticisms from the public. She shared that nobody could form an opinion on her body if they never got a good look at it.

Most recently, in an interview with the Sunday Times on June 18, Eilish shared that she is feeling a lot more confident in her own skin, and feels more freedom and confidence in choosing how to style herself. “In the past couple of months, I feel far more solid in who I am… I feel like I’m capable of being as feminine as I want to be and as masculine as I want to be.” There are very few people who could pull off a crystal beekeeper hat at the American Music Awards, and even fewer who could rock a gothic, deconstructed trench coat at the Grammys. But throughout the years, Eilish’s style has matured, serving as a strong expression of her individuality. We’ve seen her grow out of the bright, colorful XXXL graphic-print sweatsuits of her teenage years to darker, more elegantly structured monochrome ensembles.

Feast your eyes on some of Eilish’s most unique outfits ahead.