Bryan was born in Orlando, Florida in the late 1940s and soon after his family moved to Virginia. His passion for fashion began during his adolescence when he discovered the 1930s through Hollywood movies. He studied Art History at the University of Virginia and went to law school at the George Washington University before settling to New York in 1968. He worked at the Abraham and Strauss Department store in Brooklyn until 1973 when he started his career with Fairchild Publications. He was the fashion editor of Men's Wear Magazine from 1973 to 1983 and "M" The Civilized Man from 1983 to 1993, and Men's fashion director for "W" Magazine in 1993. He then joined he New York Times in 1995 until 2006. He contributed articles to the CFDA Third volume of American Fashion in 2008.