Hipsters is apparently a word that morphs along...changing with the times. Back in my youth, I pretended to be a hippie...and I think some of us were referred to as hipsters...which is what I think Paul looked like in his mugshot. As a matter of fact, Paul, you looked like one of my boyfriends.
Back in the 1950s and 60s someone in a leather jacket that might steal something out of a purse might have been a "hood" as in hoodlum...usually a black leather jacket - not a "cool" one with fringe like one of the guys in Crosby Stills Nash and Young! Before then I think leather jackets were what fighter pilots wore.
Yeah I don't dig the yellow / green combo. My friend's is blue with the white checkered stripe.
As for the F100, take my word for it. About ten years ago the trend was that first Ford Bronco from the 60's, up to about the mid 70's when it got a little bigger but still had a pull off hard top. You'd see it show up in tons of movies and TV shows. That was the go-to car style that set designers used to signal to the audience "hey this guy is cool, but he's not a show-off." Lately it's switched to 70's pickups. And hipsters like that rugged/cheap/cool-but-not-trying-too-hard look. See also: Boxy early 90's Jeep Cherokee. It cannot look too new, or expensive, or showy. It has to go very well with a lumberjack flannel shirt.
I say all this partially in jest, and partially not.