Any guitarist can relate to having to keep the noise down when wanting to play, but it was this requirement that would define Montgomery’s technique and style when playing the guitar. Having worked long hours during the day, Montgomery’s practice was limited to nighttime while his wife was sleeping. For this reason, instead of using a pick, he strummed chords with the flesh of his thumb, developing a softer and more expressive tone through the instrument. For single notes he would use downstrokes and for chords and octaves he would combine upstrokes with down.
Montgomery, as revealed in the liner notes for the album Ultimate Wes Montgomery, also had a corn on his thumb, which gave his sound what George Benson described as a “point”. “He would get one sound for the soft parts, and then that point by using the corn. That's why no one will ever match Wes,” Benson wrote in the album notes.
Having virtually no knowledge of scales or modes, Montgomery’s style became centered on the use of single note lines, octaves, and block chords when soloing, which, combined with his thumb technique, provided a full and rounded sound while maintaining his soft and expressive signature touch. It was his lack of training combined with his unusual technique that allowed Montgomery to be so innovative and influential as a jazz guitarist. According to Joe Pass, Montgomery was one of only three guitarists who were “true innovators”; the other two being Montgomery’s heroes Christian and Reinhardt.