Celebrities Who Defined Cool (24 PICS)

Heather Graham, 1990s

Frank Sinatra mixing drinks at the bar in his home, Palm Springs, California, 1965.

Tiffani Amber Thiessen, 1990s

Daryl Hall & John Oates in New York City, 1973

Sharon Tate, 1960s

Natalie Imbruglia, 1997

Rachel Weisz, 1987

Elvis Presley and Barbara Eden in ‘Flaming Star’ 1960

Betty Brosmer, 1960s

Jennifer Love Hewitt, 1998

Salma Hayek, 1995

Barbara Nichols, early 1950s

The Beatles, 1969

Julie Delpy and Ethan Hawke, 1995

Jayne Kennedy, 1970s

Mark Hoppus from Blink-182 smoking a cigarette on stage during the Dude Ranch tour, circa 1998

Jennifer Connelly, 1991

Eric Clapton with grandmother Rose Clapp in 1970 in Surrey, England.

Dian Parkinson, 1980s

Kurt Cobain & Courtney Love, 1992

Audrey Hepburn & William Holden, 1953

Marilyn Monroe, 1953

Lesley Ann Warren, Colleen Camp, and Eileen Brennan on the set of ‘Clue,’ 1985.

Stevie Nicks, 1970s