Dita Von Teese
The burlesque beauty has built a career out of rocking it old school. Dita's specialty is 50s pinup—curve hugging dresses, elegant accessories, black curls and red lips—and she never breaks character.
Chloë Sevigny
The Big Love star is a fashion risk taker andon this occasion it pays off. Chloë strikes a Twiggy-esque pose in a mirrored mini and blond shag. It may even look like 60s vintage but the actress didn't dig this mod piece out of the archives—it's modern-day Miu Miu!
Jordin Sparks
With her gorgeous curves, the Sparkle star is a natural for 50s-style cinched dresses with fitted tops and full skirts. But Jordin's red carpet style choices have already shifted a decade after starring in the 60s period piece.
Nicole Richie
The reality star turned designer can't resist a long, flowy maxi dress, all a part of her signature boho style. Even better if she can pair the look with some oversized shades or a funky headband to further personalize the look.
Ashley Olsen
What does the woman who can afford anything prefer to buy? Vintage, of course! Ashley loves to dip into the archives for one-of-a-kind red carpet looks, like this late 70s / early 80s orange gown with substantial shoulder pads and delicate gold stitching.
Zooey Deschanel
The New Girl star looks like a prom queen plucked from Back to the Future. Zooey tends to add a touch of 50s-style sweetness to her outfits with full skirts, bangs and bouffant hairstyles, without wearing so much that it becomes costume-y.
Heidi Klum
She's so tall and willowy that the Project Runway host is a natural for a leggy, 70s-style pantsuit or jumpsuit. After all, who but Heidi could pull off this brown silk halter suit from Michael Kors?
Olivia Munn
The Newsroom star tapped her inner glamour gal for this retro screen queen style. From the pencil skirt, slinky camisole and towering platforms to her loose black curls and pop of red lipstick, Olivia's a young Elizabeth Taylor look-alike.
Katy Perry
Today a Jazz Age flapper—complete with satin gown, wavy bob and strands of pearls—tomorrow a 50s pinup girl. The Pieces of Me star loves to have fun with her look, flitting from one decade to another all while looking fabulous.