Bostonian Oakes apprenticed with well-known Arts & Crafts jeweler, Frank Gardner Hale, and established his own studio in 1918. He earned a medal from the Boston Society of Arts & Crafts, where he was one of the longest-standing members. His handmade pieces are known for their exquisite craftmanship, employing curling leaves and wirework and notched frames. The Metropolitan Museum of Art and the Museum of Fine Arts, Boston include Oakes pieces in their permanent collections.