In 1982 NSI asked Halston to design a range for the downscale J.C. Penney department stores. He agreed, but the decision had unanticipated, severely negative consequences. Bergdorf's dropped his collections and formerly faithful friends and clients defected to other designers. Halston's relationships with his bosses and colleagues deteriorated until finally he was locked out of his offices after throwing a tantrum.

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His career shattered and his health failing, Halston retired from the fashion world. In Simply Halston, Steven Gaines notes that "Halston would live the rest of his life in self-imposed exile, an Elba of his own creation. The man who was only as good as the people he dressed ended up not dressing anyone."

Halston was diagnosed with AIDS in 1988. He died of AIDS-related lung cancer in San Francisco, California on March 26, 1990.

Since his death the House of Halston has hired a number of creative directors. Under the direction of Randolph Duke the House became well known once more for evening wear. More recently, under the leadership of Craig Natiello, the House returned to the classic Halston lines (including the Ultrasuede shirtdress) and enjoyed a revival of its reputation. The current designer at the House of Halston is Bradley Bayou, who is known for his extravagant gowns.

The association between homosexuality and fashion is multifaceted, ranging from the role of clothes as signifiers of sexual orientation to the immense contributions gay men have made at all levels of the fashion industry.

American designer Calvin Klein has created an extraordinarily successful fashion empire through his simple and elegant designs and his skilful employment of provocative advertising campaigns that are saturated with homoeroticism.

The avatar of Pop Art, Andy Warhol expressed desire in his images of celebrities and flouted traditional notions of masculinity by embracing extravagance, effeminacy, and an obsession with surface appearances.