Cunningham was born and raised in Boston, where he had his first exposure to the fashion world as a stockboy in Bonwit Teller's Boston Store. After attending Harvard University briefly, he dropped out in 1948 and moved to New York City at the age of 19, where he worked again at Bonwit Teller, this time in the advertising department. Not long after, he quit his job and struck out on his own, making hats under the name "William J." This business folded when he was drafted during the Korean War. After serving a tour in the U.S. Army, he returned to New York in 1953 and started writing, first for Women's Wear Daily and then for the Chicago Tribune.
Cunningham photographed people and the passing scene in the streets of Manhattan every day, focusing on their genuine usage of clothing to express personal style. He was known not to overly photograph celebrities (as paparazzi would) or people that use fame to showcase clothing they did not originally pick themselves (sponsored, free clothing). Most of his pictures, he has said, are never published. His personal independence philosophy was: "You see if you don't take money, they can't tell you what to do, kid." Designer Oscar de la Renta has said, "More than anyone else in the city, he has the whole visual history of the last 40 or 50 years of New York. It's the total scope of fashion in the life of New York." He made a career taking unexpected photographs of everyday people, socialites and fashion personalities, many of whom valued his company. According to David Rockefeller, Brooke Astor asked that Cunningham attend her 100th birthday party, the only member of the media invited.
In 1978, he published Facades, a collection of 128 photographs of Editta Sherman in front of significant Manhattan buildings.
In 2014, a collection of his photograph were exhibited as "Bill Cunningham: Facades" at the New-York Historical Society,
In 1983 the Council of Fashion Designers of America named Cunningham the outstanding photographer of the year. In 2008 he was awarded the Officier de l'ordre des Arts et des Lettres by the French Ministry of Culture. In 2009, he was named a living landmark by the New York Landmarks Conservancy. In 2012 he received the Carnegie Hall Medal of Excellence.
In 2010, filmmaker Richard Press and writer Philip Gefter of The Times produced Bill Cunningham New York, a documentary about Cunningham. The film was released on March 16, 2011. It shows Cunningham traveling through Manhattan by bicycle and living in a tiny apartment in the Carnegie Hall building. The apartment has no closet, kitchen, or private bathroom, and is filled with filing cabinets and boxes of his photographs. The documentary also details his philosophy on fashion, art and photography, as well as observes his interactions with his subjects while taking photos.
Cunningham was featured on BBC Two's The Culture Show in March 2012.
Cunningham died in New York City on June 25, 2016, after being hospitalized for a stroke. He was 87.
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