He showed his first collection in 1981, which was bought by the department store Neiman Marcus.
In 1988, he moved to New York and launched his "Times 7" line which featured unusual buttons and accessories. In 1989, a womens wear line was produced.
Oldham disavows kitsch, an almost inescapable epithet for his idiosyncratic talent, but his enthusiasm for naive crafts and his juxtapositions of good and highly uncertain taste encourage the description, however inadequate. Kitsch implies, however, no intervention or interpretation, only laconic appropriation. Oldham's aesthetic power is a willful perversity, a zest for twisting and changing the original source, whether kitsch or Mediterranean mosaic. His buttons are curious and quirky; his well-tailored suits are saved from conformity by their odd pockets; and his canny knowledge of fashion sources is saved from being scholastic by his whimsical juxtapositions.
For all of its personal taste, Oldham's fashion extends the tradition of Schiaparelli in its bold thematic development, delicate equilibrium between propriety and aesthetic anarchy, overt decoration, and annexation of related arts.
Oldham's aesthetic is bold and self-assured but far less transitory than it might initially seem. Oldham's creativity is in tune with fashion's constant striving to achieve ironic involvement in matters outside of dress and attempts, with irony, to understand the phenomena of clothing and contemporary life.