September's Shadow creates somber melodic music that spans several styles. Their debut album, Hobson's Journey, is primarily a synth pop endeavor that weaves catchy hooks with experimentation. The music combines electronic sounds along with acoustic guitar work and vocals to deliver a feeling of longing. The music expresses several moods and carries listeners to someplace familiar. September's Shadow is primarily the work of David W. Jacobsen, more commonly known for his singer/songwriter projects. Additional vocals were provided by KT Wills and Stefanie Seskin.