The Dead Boys' Club (1992)

It's the 1990s. Toby, just out of college in Wisconsin, comes to Manhattan to spend the summer with his older cousin, Packard, a gay man whose lover John R. has just died of AIDS. Toby is shy, the openly-gay society around him makes him nervous. Packard gives Toby a pair of John R.'s shoes; when Toby puts them on, he has powerful visions of the pre-AIDS scene in the 1970s, as if he's there. He also takes on a different personality when he wears the shoes, more sure of himself, able to express his interest in men. Wearing the shoes, Toby goes to a bar, hooks up with Dick, and wakes up in Dick's bed. How will he handle it? And what will happen to the shoes?