I recall back in the late 1980s there was this young guy in his early 20's who had a crew-cut, wore plaid shirts like the 'Beaver' did and wore Khaki pants.
I was still in my 30's at the time and this one lady, who was around 35 asked me one day "Why is that young man dressed like an old man and why does he wear his hair like an old Man?"
I said "hell if I know" and laughed about it.
this was when glam metal was still the rage and most guys his age had at least shoulder length hair, but this guy stuck out like a soar thumb and looked like he came out of the 1950s.
I got to talking to him one day and found out he was into Rap music and did not like Rock at all so ever since that day I have placed some of the blame on the return to 1950s haircuts on Rap performers and especially the Beastie Boys who helped usher in that look with the buzzcut and backwards baseball cap.
there were also some nerdy acts during the same period who might have contributed to the nostalgic return to the 1950s such as the
group "They May Be Giants", who I always perceived as more of a novelty act so I think there influence was probably rather limited. I think 'Barenaked Ladies', one of the dorkiest of the mainstream acts to come along in the past 20 years probably were influenced by them though. lol
anyway, there is always that saying "What comes around comes back around again" and if they brought the 1950s back then it's highly probable that the 1960s and 1970s are on the rebound so period hairstyles, I.E, LONG hair is definitely on coming back in because it's time to give the repeat of the 1950s a rest!
stay tuned.........
~Peace and Love~
Jerry aka Old Hippie