This really started when a local radio personality posed the question of where “hippie” comes from. I thought, of course Herb Caen always claimed to be the original coiner of the word. I couldn’t find any authoritative discussion or cites in a cursory glance through Word Detective and ADS. No Big List entry here. Perhaps it’s just too obvious a derivative of “hip.” But I’d have to take issue with AHD and others that “aware” of fashion or meaning (hip to the jive) is the central defining feature. Maybe it was so at the beginning of the word usage, but in my lifetime the concept of hip has meant more being at the cutting edge and embodying the spirit of something that always recognized but never explicable. Not that I know from personal experience.*
Dude of course is another etymological hobbyhorses, but I wonder if it’s ever been connected with “duds” as in clothing?
*I am certainly “aware” of fashion and meaning, but few have ever accused me of being hip.