Oldham's father, Andrew Loog, was a United States Army Air Forces lieutenant, a Texan of Dutch descent,[REF] who served with the Eighth Air Force.
A self-proclaimed hustler who spent teenage summers swindling tourists in French towns, Oldham's interest in the pop culture of the 1960s and the Soho coffeehouse scene led to working for Carnaby Street mod designer John Stephen and later as an assistant to then-emerging fashion designer Mary Quant.