Claire Standish: Love her or hate her, she's the quintessential '80s princess you either wanted to be or wanted to run over (but still... wanted to be). Played by
Molly Ringwald, she is forever remembered for dropping gems like, "Do you know how popular I am? I am so popular. Everybody loves me so much at this school," she eventually redeemed herself by crossing social battle lines to hook up with the outcast Bender (
Judd Nelson) and giving Allison (
Ally Sheedy) a compassionate, less invasive version of "The Swan" in the girls' bathroom. Yet it's her clothes, maybe more than her status, that we coveted. Classic rich yet understated WASP/prep style: knee-length
tweed skirts, lace-up
riding boots, and layered tops paired with leather accessories. With the '80s back in full-force on the Fall 2009 runways, jump on the trend early-- or just if you're feeling nostalgic-- and cop Claire's look by clicking the slideshow.