Stewart was born in Springfield, Missouri, and attended Southern Methodist University in Dallas, Texas, where he was a member of Phi Gamma Delta. He was always popular with fans, especially for his clothing, and was reputed to have the biggest wardrobe of all professional golfers. He was a favorite of photographers because of his tam o'shanter caps and patterned trousers, which were a combination of plus fours and knickerbockers, a throwback to the once-commonplace golfing "uniform".