I think it's another "every generation feels the next is dumbner for not knowing things" paired with the fact that it's always true and we are probably consistently getting dumber year to year.
Old people made fun of me for knowing nothing about cars or the civil war generals, and now we get to make fun of them for computers.
Even our "dumb college students" stereotypes are getting dumbner. Compare this freshman of philosophy: https://youtube.com/watch?v=57vCBMqnC1Y
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Coolness is associated with freedom and relaxation and confidence yes. So caring less about what others think is usually cool, but the neurotic person dutifully buckling seatbelts for a 5 minute pickup jaunt is not cool. (not to say they aren't cool in general, just in this specific moment. they could very well be cool to give a moving eulogy when a drunk driver ends the merry ride early for anyone not wearing a seatbelt)
I've used some adjectives to stack the deck unfairly here of course, because this pup would be cooler than a try-hard wannabe that would like to buckle seatbelt but avoids doing so because they care so much about what other people think.
There's something about the fact that the doing (seatbelt) is uncool and the actively-non-doing (unbuckling to fit in) is double-uncool and the passive-non-doing (jaunt) is the cool thing.
Additionally: consider proportionality of safety-ism. Teen wearing a helmet for a razor scooter is uncool. Neil Armstrong triple-checking industrial buckles is very cool. (source: my opinion). Whether wearing a seatbelt is cool or not depends on which reference class a car-ride feels like.
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