Film / Series

Steve McQueen · The Thomas Crown Affair

Glen check three-piece suit

Faye Dunaway · Bonnie and Clyde

Cream button-front dress

Audrey Hepburn · Breakfast at Tiffany's

Wide-brim hat and black dress

Cary Grant · North by Northwest

The grey suit

Cary Grant · To Catch a Thief

Midnight dinner suit

Marilyn Monroe · The Seven Year Itch

Embroidered cocktail dress

Audrey Hepburn · Sabrina

Embroidered strapless gown

Grace Kelly · Rear Window

Black bodice and tulle skirt

Audrey Hepburn · Roman Holiday

Off-shoulder brocade gown

Marilyn Monroe · Gentlemen Prefer Blondes

Pink strapless gown and gloves

Gene Kelly · Singin' in the Rain

Rain-soaked suit and fedora

Rita Hayworth · Gilda

Embroidered crop top and column skirt

Humphrey Bogart · Casablanca

White dinner jacket

Katharine Hepburn · The Philadelphia Story

Beaded bodice and chiffon gown

Vivien Leigh · Gone with the Wind

Burgundy gown with feathers

Fred Astaire · Top Hat

White tie and tails

Marlene Dietrich · Morocco

Top hat and tailcoat