Dobbie Gillis was a 1950s, early 60's "preppy" dresser, everyone was, button downs, kalkis or 501s and weejuns or split toe loafers. I think you are thinking of Maynard G.Krebs.
I never thought of Dylan as a hipster
Every normal man must be tempted, at times, to spit on his hands, hoist the black flag, and begin slitting throats.
H. L. Mencken
