Jazz theory is deeply cumulative: you cannot understand reharmonization until you understand chord scales, and you cannot use chord scales until you know how chords and voicings work. Skip a rung and the advanced books read like nonsense. A careful order fixes that, and it pairs naturally with instrument practice and ear training, since theory only becomes music when you play it. This path runs from the standard reference to the frontier.
Start with the book almost every player owns, then branch into application and depth.
The core reference
Begin with The jazz theory book by Mark Levine, the near-universal starting text that covers scales, chords, and progressions clearly, and Jazzology by Robert Rawlins, a well-organized companion that fills in fundamentals. If you play keys, The jazz piano book, also by Levine, translates the theory directly into voicings under your hands.
Deepen your harmony
With the basics solid, go deeper into how harmony actually works. Harmonic Experience by W. A. Mathieu explores the roots of tonality in a way that reshapes how you hear, and Connecting Chords with Linear Harmony by Bert Ligon reveals the voice-leading lines that make bebop flow. Reharmonization Techniques by Randy Felts then teaches you to reharmonize a tune yourself, a key creative skill.
Advanced concepts
Finally, take on the ambitious systems. The Lydian chromatic concept of tonal organization by George Russell is a foundational and demanding theory of tonal gravity that influenced generations, Jazz improvisation by John Mehegan offers a systematic method, and The Music of Bill Evans by Brent Edstrom lets you study a master's harmony in detail.
Read in this order, each book prepares the next, and none of it feels like a wall. Follow the full path, and keep an instrument nearby the whole way.