Cheslow was influenced by the Beatles, Yoko Ono, Patti Smith, The Slits, Teenage Jesus and the Jerks, and jazz. Her first band Chalk Circle, as guitarist, grew out of her friendships with Anne Bonafede, Henry Garfield (later Henry Rollins), and members of the Teen Idles and Untouchables around late 1979/early 1980. They shared a love of Bad Brains and California punk. When the D.C. hardcore scene became more macho and male-dominated, Chalk Circle didn't fit in and were put down for being all girls. But they got support from art punk bands such as Half Japanese and Velvet Monkeys. Cheslow attended University of Maryland and first learned about feminist theory through film studies classes with Robert Kolker. These experiences led Cheslow to examine and write about the role of women in music.