Silverstone was born in San Francisco, California, the daughter of Deirdre "Didi" (née Radford), a Scottish-born former Pan Am flight attendant, and Monty Silverstone, a real estate agent born in England. She has two older siblings, a half-sister from her father's previous marriage named Kezi Silverstone and a brother named David Silverstone. She grew up in an upper-middle class home in the San Francisco suburb of Redwood City, California.[citation needed] Her father is Jewish and her mother converted to Conservative Judaism before marriage. She began modeling when she was six years old, and was subsequently cast in television commercials, the first being for Domino's Pizza. She attended Crocker Middle School and then San Mateo High School
Silverstone won several awards for her film performances. She received multiple MTV Movie Awards and a Young Artist Award for The Crush. For Clueless she received multiple MTV Movie Awards and a Young Artist Award once again, plus awards from Blockbuster Entertainment Award, Kids' Choice Awards, National Board of Review, and an American Comedy Award.