Stephens was born in New York, but spent his summers with his brother Roderick (Rod) Stephens, Jr, learning to sail on the New England coast. He also attended the Massachusetts Institute of Technology for one term.
Entered the marine industry at an early age, Olin apprenticing in yacht design under Phillip Rhodes. With his father’s backing, the 21-year old Olin entered into a partnership with the already successful yacht broker Drake Sparkman, and Sparkman & Stephens, Inc. was formed.
Months after opening for business, the financial crisis of the Great Depression swept the global market. In spite of this, Stephens’ father ordered a design for a racing yacht from the young firm – a yacht named Dorade. As her first major test, Dorade won the much-publicized 1931 Trans-Atlantic Race. That victory launched the design reputation of Sparkman & Stephens – and set a course for the firm that would last more than half a century.
The Stephens’ name would later become synonymous with the America’s Cup, having designed six out of seven successful 12 Metre defenders of the America’s Cup between 1958 and 1980, with the exception of Weatherly in 1962.
Stephens was also involved in ocean-going sailboats. His yawl designs Dorade (1929) and Stormy Weather (1934), his favorite design, each won the Newport Bermuda Race and the Fastnet race several times.
Together Olin and Roderick Stephens formed a team that had a major worldwide influence in yacht design, creating racing and cruising designs that helped to popularize the sport. Since the establishment of Sparkman & Stephens, the firm has completed over 2750 designs and related assignments in the pleasure, commercial and military sectors.
In 1993, Stephens was inducted into the America’s Cup Hall of Fame and awarded the Gibbs Brothers Medal from the National Academy of Sciences. Several years later, in 1999, he wrote the autobiography All This and Sailing Too. In 2007, he was named as one of six inductees to the inaugural ISAF Sailing Hall of Fame. He was ranked member number 1 on the New York Yacht Club Member Seniority List at the time of his death. Stephens died exactly five months after celebrating his 100th birthday in 2008.