CONSIDER YOUR OPTIONS
Given that Montgomery’s sound set the template for octaves in jazz guitar, many players choose his preferred method of articulation as a default position, brushing across the strings with the thumb to produce an exotic and breathy tone that is both warm and strident. Both Django Reinhardt and Jimi Hendrix liked to strum octaves with the plectrum, although you need to be extra careful muting extraneous strings here. John Scofield adopts a hybrid pick-and-finger approach with great success so naturally you could choose to dispense with the plectrum all together and pluck both notes with a combination of thumb and finger. Remember that there’s no reason why you need to pledge allegiance exclusively to any one approach, so feel free to mix up your articulation options depending upon the musical scenario, the tone that you’re after and the intricacies of the specific part you’re aiming to deliver.