Marilyn Monroe. Audrey Hepburn. David Bowie. Madonna. The list of fashion's greatest influencers is as compactly diverse as it is iconic, but few have succeeded in earning the inarguable title of "style icon." Prince is one of them.

From the striking glitz of disco glamour to the idyllic luxury of new romanticism and the sexually empowered swagger of sleek '90s power-dressing, the late Prince was an enigma of sartorial proportions. The artist transcended trends, instead blazing a trail of timeless fashion statements onstage and onscreen through the decades — leaving a blur of lace, glitter, and floral prints in his fabulous wake.

As a style icon, he was much more than just fashionable — he was progressive. Along with David Bowie, another music-style game-changer from his era, Prince redefined the very idea of what made a man sexy. He helped to redesign cultural attitudes about sexuality, symbolizing — quite literally at one point, as he changed his name to an actual symbol in 1993 — the unrestricted junction between masculine and feminine, exploring that territory with the unbridled freedom of his oft-gender bending manner of dress.

The prolific musician perhaps most affectingly embodied the aesthetic breaking of socially-constructed gender boundaries on the floral cover of his 1988 album, Lovesexy. Appearing nude in a traditionally feminine pose — back slightly arched, arm draped across his chest demurely — the artist oozed barrier-free sex appeal in artwork that was so offensive (to some) that many record shops were forced to wrap the LP in black plastic just to display it on shelves.

Artwork courtesy of Paisley Park Records / Warner Bros.

"I am something that you'll never comprehend," Prince once sang. The words remain truer than ever following his untimely passing, and the sentiment lives on in all of his incredible style statements that we'll never forget.

Revisit ten of Prince's most iconic fashion moments in our gallery, above.