The proposed essay focuses on a piece of costume that is often both dirty and worn out: the man’s leather boot. The boot has been a constant in cinema, appearing first in Westerns films made at the beginning of the 20th century. As an iconic piece of male costume, the boot has populated male-oriented genres, signaling either masculinity en masse (as in war films), or a kind of masculinity closer to nature and to animals than to civilization (as in the Western film). Departing from earlier scholarship on masculinity as spectacle (e.g. Tasker; Holmlund), and engaging in textual analysis, this essay investigates how the boot, as a hyper male piece of costume, can be read as a masquerading prop, and as a tool for hiding (what is not there). Films to be analyzed include Lives of A Bengal Lancer (Henry Hathaway, 1935); Picnic (Joshua Logan, 1955); Midnight Cowboy (Johan Schlesinger, 1969); and Blaze (Ron Shelton, 1989).