Barritt attended MSA and the Saltus Grammar School in Hamilton, Bermuda.[1] He moved to New Brunswick, Canada, to study fine arts at Mount Allison University in Sackville.[1] In 1950, Barritt returned to Bermuda to take a position at his family's ginger beer business, John Barritt & Son Ltd.[1] However, he continued to paint, specialising in oil paintings.[1] Many of his paintings focused on Bermuda's Civil Rights Movement.[1]
Barritt was one of a small group of white Bermudians who spoke out in favour of universal suffrage of the island.[1] He joined an all-Afro-Bermudian basketball team to draw attention to desegregation efforts.[1]
Despite his involvement in social issues, Barritt remained reluctant and "unsure" about politics.[1] He did not join the United Bermuda Party (UBP) until 1972.[1] In 1985, Barritt and fellow UBP candidate, Lawson Map, were elected to the House of Assembly of Bermuda from the Pembroke East Central constituency.[1][5] The election marked the first, and only, time that the UBP held the Pembroke East Central seats in the House of Assembly.[1] Barritt served in House of Assembly from 1985 until 1989.[2]
Barritt also served as the Minister of Community and Cultural Affairs under Premier John Swan during his tenure in the Assembly.[1][6] He was later appointed as a UBP member of the Senate of Bermuda.[1]
Robert Barritt donated three of his paintings to the Bermuda National Gallery. His three works gifted to the National Gallery were ; Theatre Boycott, Upstairs Right (1959), Two Weeks Before Christmas and Government House (1960), and Descent from the Cross (1961).[1][6] When describing his paintings in 2008, Barritt said, "I'm a painter of the three R's. Not reading, writing and arithmetic. Rum, race and religion."[1] Gary Phillips, Chairman of the Bermuda National Gallery, has described Barritt's as imbued with a "sense of 'equality, tolerance and peace'."[6]
Robert Vaughn Barritt died on June 21, 2015, at the age of 88.[1] He was predeceased by his late wife, Grace Elizabeth Barritt. Premier of Bermuda Michael Dunkley and former Premier John Swan paid tribute to Barritt following his death.[6]