From The Jargon File (version 4.4.7, 29 Dec 2003) :
propeller head n. Used by hackers, this is syn. with geek. Non-hackers sometimes use it to describe all techies. Prob. derives from SF fandom's tradition (originally invented by old-time fan Ray Faraday Nelson) of propeller beanies as fannish insignia (though nobody actually wears them except as a joke).From The Free On-line Dictionary of Computing (30 December 2018) :
propeller headUsed by hackers, this is synonym with computer geek. Non-hackers sometimes use it to describe all techies. Probably derives from SF fandom's tradition (originally invented by old-time fan Ray Faraday Nelson) of propeller beanies as fannish insignia (though nobody actually wears them except as a joke). [{Jargon File] (1995-01-18)