carly
simon

"You're so vain," Carly Simon crooned in her immortal chart-topping 1973 hit of the same name, but the Grammy Award winner herself has never been known for preening: Despite an aristocratic upbringing—her father co-founded the Simon & Schuster publishing company—the singer-songwriter epitomized a natural, breezy seventies style with her wild mane of hair, sun-kissed skin, rockin' body, and that preternaturally wide smile.

Simon's iconic earthy look captivated some of the era's most famous men. Her list of romantic conquests includes Cat Stevens, Warren Beatty, Mick Jagger, and James Taylor, the last of whom she was married to for 11 years. It also landed her fashion spreads in the pages of Vogue. Now, with the seventies having a major moment on the runways and the songstress herself on stage at this summer's Lilith Fair, Simon is back in the spotlight. (Wouldn't you just kill for the caftan she's wearing in slide 2?)

—Kara Jesella