Discovered as a model by talent manager Jean Renard, Ocleppo Hilfiger turned to design at the encouragement of her husband, Tommy Hilfiger, who steered her toward a line of vintage-style luxury handbags under her own name. She credits Lauren Hutton, Grace Kelly and her friend Iris Apfel among her stylistic influences.
Launched in 2012, the label sold its first handbag to Harrods before opening showrooms at Trump Tower in Manhattan and at Galeries Lafayette in Paris. In 2015 she introduced Bag Bar, a custom accessory system for classic handbags, later acquired by Kate Spade; in 2017 the brand partnered with Judith Leiber, with Ocleppo Hilfiger becoming its creative director.