Just like her on-screen alter ego once sang, when it comes to her sense of style, Miley Cyrus is all about having “the best of both worlds.” Equally talked-about for her unique aesthetic when she’s off-duty as the looks and outfits she chooses for the red carpet and the stage, this chart-topper has been influencing how her followers get dressed since she was just a tween.

From the moment she entered the spotlight during her Disney channel heyday, Cyrus has gone through no shortage of fashion iterations—from rock princess to provocateur and country music belle to indie icon. But thanks to a long-time collaboration with her award-winning stylist Bradley Kenneth over the last decade, the Tennessee native has transformed into a veritable fashion plate with whom luxury brands are clamoring to work.

The proof was in the pudding recently at the 2024 Grammys, where Cyrus was the most celebrated artist of the night, having finally received not one but two awards from the Recording Academy. For her milestone career highlight, the star changed outfits at a dizzying pace — rocking a total of five unforgettable outfits. One such look was a vintage Bob Mackie minidress from 2002 worn for her impressive performance, which led to an unforgettable image of an empowered pop star at the top of her game.

This latest chapter in her style journey has also seen her land coveted campaigns with Dolce & Gabbana, Gucci, and Marc Jacobs. Thanks to Cyrus and Kenneth’s inimitable mix of genres, references, and eras, her music videos and album art are dissected by eagle-eyed fans.

While fans are eagerly camping out to get updates about what the selective star is going to do next, professionally and personally, here’s a look back at some of Miley’s most memorable moments in the style stakes as we await whatever surprise she’ll have in store for us next.