“Bootless” means hopeless or useless. It invokes connotations of poverty and a lack of material possessions. In characterizing his “cries” to heaven as “bootless,” the speaker suggests that his cries go unheard because they are poor, impoverished, or lacking. This claim is slightly ironic, however, as the Christian tradition believes that a lack of material wealth makes a person more pious and close to God. Despite the spiritual backdrop of poverty equating to piety, the speaker’s lack of material or social wealth does not afford him any religious salvation. As will become clear later in the poem, he sees the love object as redemptive.