(Photo: Melissa Hom)

Scarlett O'Hara
Fille de Joie is the place to go for frilly, feminine frocks and vampy vintage looks, including an array of tutus and skimpy slip dresses. The store's Scarlett O’Hara gown ($200) is a surefire hit for those willing to go all out, hoop skirt and all. In the same vein, we came across a full-skirted lacy pink dress at David Owens that could conjure up a passable Glinda from The Wizard of Oz.

Don Draper
The Mad Men look provides a sharp, swanky getup for the guy who would rather collect a few phone numbers on Halloween than win a costume contest. And though it’s a fairly easy outfit to replicate, vintage shopping ensures that you do it right. At Fabulous Fanny’s, suspenders are available by the dozens ($20), rows of feathered fedoras emanate old-school style ($45), and the ties are true sixties relics ($15).