A major part of Penn's work for Vogue consisted of portraits of celebrities, artists, writers, and other personalities relevant to the reporting valued by the magazine. They constitute a true encyclopedia of twentieth-century cultural history. For his first extensive portrait campaign, he set up unusual environments in the studio for his sitters to insert themselves into and react against: a constricted corner space made of two walls placed at an angle, and a tattered carpet draped over a solid base they could sit on. These point to Penn's interest in disruption, present in his early work for the magazine as he attempted to give his images a grittiness that would animate the page.

This practice allowed Penn to refine his ability to produce the environment without anything more than a backdrop and a stool. Always one to eschew ornate backgrounds that could distract from the subject, in his portraits Penn sought to distill the essence of his subject.  When discussing his portraiture, he framed it as an attempt to find a person at a moment of calm, when they allowed the facade to fall away.