Klein entered into a jeans licensing agreement with the Puritan Fashion Company in 1977 and in 1980 he introduced his designer jeans in a 1980 commercial where 15-year-old Brooke Shields was paid $500,000 to suggest she was panty-less when she uttered “Nothing comes between me and my Calvin’s.” 200,000 pairs sold in the first week! Sales of designer jeans peaked in 1982 and in 1983 Klein bought back his jeanswear license from Puritan fashion for 60 million.

Klein’s next big success story was the reinvention of underwear. In 1984 he unveiled a huge billboard in Times Square bearing a well-toned young male model wearing nothing more than Klein’s new sexy re-invention of classic ’tighty-whities’ and an appendectomy scar. Gender-bending boxer shorts for women soon followed. Not to be outdone, the following year in 1985 Klein released his first fragrance, Obsession, with a ads featuring a slew of carefully posed nude models. Klein signed a pact with Marchon Eyewear in 1991 to make Calvin Klein eyewear first put on sale in 1992.

Klein’s long run with success started to go rocky the same year when pal David Geffen bailed the company out of 62 million in junk bond debt inherited from the Puritan buyback and also helped Klein license his underwear business to Warnaco. Global licensing expanded in the early 90s but Klein was losing his older, established clientele who had followed his designs throughout the 70s and 80s. Klein drew huge criticism for using models who looked underage, underfed and drugged out in 1997. His new advertising campaign in 1998 focused on healthier looking models but when he used children in an underwear campaign in 1999 he had to withdraw his print and film ads under accusations of promoting child porn. Klein shopped around for a merger or buyout in 1999 but after talks with Tommy Hilfiger failed, he took the company off the market in 2000.

Things went from bad to worse when Klein filed suit against Warnaco accusing it of selling full-price merchandise in discount outlets, settling out of court in 2001, the same year he cut his staff by 10% and shut down his CK mid-priced sportswear division (the last business that was manufactured by the company itself.) Phillips Van Heusen acquired Calvin Klein in early 2003; around the same time that Klein created an embarrassing public display at a basketball game where he seemed despondent. Barry Schwartz left the company and Francisco Costa replaced Calvin Klein as head designer in 2003.