From PEOPLE Magazine Click to enlarge
THE LOOK: HIPPIE

FLASHBACK: Ali MacGraw 1970

NOW: Jenna Dewan-Tatum

THE LOOK: LADY-LIKE

FLASHBACK: Princess Diana 1982

NOW: Penélope Cruz

THE LOOK: ROYAL

FLASHBACK: Princess Grace 1956

NOW: Kate Middleton

THE LOOK: LBD

FLASHBACK: Demi Moore 1991

NOW: Halle Berry

THE LOOK: CLASSIC

FLASHBACK: Jackie Kennedy 1960

NOW: Kim Kardashian

THE LOOK: ROCKER

FLASHBACK: Madonna 2000

NOW: Evan Rachel Wood