Richardson has shot campaigns for Marc Jacobs, Aldo, Supreme, Tom Ford, and Yves Saint Laurent among others. He has also done magazine editorials for publications such as Rolling Stone, GQ, Vogue, Vanity Fair, i-D, and Vice.
There are several repeating themes in Richardson's work, notably that of putting high-profile celebrities in mundane situations and photographing them using traditionally pedestrian methods, such as the use of an instant camera.
His work also explores ideas of sexuality, with many of the pieces featured in his books Kibosh and Terryworld depicting full-frontal nudity and both simulated and unsimulated sexual acts.
Initially, many of Richardson's subjects would be shot before a white background but he eventually expanded to other backdrops. He is also well known for posing with his subjects, often trading his trademark glasses with them so they may "pretend to be him" and vice versa.