Sylbert began his career in the early days of television, designing productions of Hamlet (1953) and Richard II (1954) for the Hallmark Hall of Fame.

He went on to design Baby Doll, A Face in the Crowd, The Fugitive Kind, Murder, Inc., Splendor in the Grass, Walk on the Wild Side, Long Day's Journey into Night, The Manchurian Candidate, The Pawnbroker, Lilith, Who's Afraid of Virginia Woolf?, The Graduate, Rosemary's Baby, Catch-22, Carnal Knowledge, Chinatown, Shampoo, Reds, Frances, The Cotton Club, Tequila Sunrise, Dick Tracy, The Bonfire of the Vanities, Carlito's Way, Mulholland Falls, My Best Friend's Wedding, and Trapped.

His widow gave the committee permission to name the award after him in perpetuity and that year it was given to Harold Michelson, his longtime art director and colleague.

Sylbert died of cancer at the age of 73 at the Motion Picture & Television Country House and Hospital in Woodland Hills, California.

At the time of his death, Sylbert was married to Native American poet Sharmagne Leland-St. John, mother of one of his daughters, Daisy Alexandra Sylbert-Torres, a costume designer and Echo Park boutique owner.