Osborn briefly ran a men's clothing and antiques boutique in Beverly Hills, California before joining Neiman Marcus where he also worked as a buyer for six years before being appointed vice-president of men's tailored clothing.
[3] Osborn helped introduce Italian menswear lines such as Zegna, Brioni, and Kiton to the American market in the 1980s.
[4] On questions of fashion, Osborn was often sought out by reporters to comment for articles in The New York Times,[5] The Wall Street Journal, and other publications.
In addition to influencing fashion through his position, Osborn was known for his eccentric personal style, identified by his mustache, wearing of wide-brimmed hats, and boutonnieres.
Osborn was featured in magazines such as GQ, Vogue Hommes, and Esquire.