Gypsy Jazz guitar was invented by Django Reinhardt. It has a complete different set of rules (and a different sound) from any other form of jazz. It has to do with chords, rhythms & note choices, BUT ALSO it owes much of it’s sound to the type of guitar used and how it is played. A Gypsy Jazz guitar has a smaller sound-hole and has a more “tinny” sort of tone. Part of this “tinny tone” is due to the natural sound of the guitar and part of it is due to the right hand picking very near the bridge.
Just listen to 3 or 4 Django songs and you’ll get it. Thousands of guitarists have spent the better part of the last 70 years trying to capture his magic. Very few have come close. After you check out Django, google Robin Nolan. He is the premiere online teacher for all things Gypsy.
Cheers!
PG