My wife has cut my hair since we were married, and in the years before that, the fashion was to avoid the barber as much as possible. I must have gotten my hair cut somewhere between 1971-1976, in Sudbury, Williamsburg, or Manchester, but I don't remember a one of them. My knowledge of barbershop culture comes from childhood. But whatever went on in these outposts of male culture was not readily shared with the young. I heard somewhere that barbers had connections to bookies, so if you ever wanted to put down a bet, that was the place to go. But whether that was all barbers or merely some of them I never knew. There was also a barber college downtown where you could get your hair cut much cheaper. Whether they taught how to be a bookie on the side at that college I never knew either. Also, did they make suggestions for what magazines you were supposed to put out, or did they let you figure that out on your own? There were sports magazines, including old-style ones like boxing or horse racing, and true crime or vaguely racy ones. Not Playboy, but Man's Life, or Argosy.
The shop's were called by the owner's first name, not by any "Supercuts" or hair stylist name. I went down to Louie's until sixth grade, except for the years that my mother tried to do it herself. Adult males who worked in offices would get their hair cut weekly. Occasionally I would see one getting a shave as well. I always figured those guys must be rich. Of course, everyone looked rich to me then as the child of a single mom in the 1960s. When she remarried a more prosperous (and eventually wealthy) man, I was deeply impressed when we moved in that everyone had his own washcloth. He got his haircut every week, downtown.
Junior high and highschool my friends and I went to Roy's if it was allowed, or Stan's if we had to. Roy would cut it the way you asked, but cleverly enough that your parents couldn't quite object. Stan was older, and after you told him what you wanted would say "I make you look good," and do what he wanted. You could actually tell at school which boys got to go to Roy's and which to Stan's. And even more, you could tell which kids had their dad put a bowl on their head every Saturday and cut it himself. But despite the general cruelty and teasing of boys that age, there was nothing but pity or commiseration about haircuts. It was a war between our parents' culture and our own. Your losses were our losses, and your victories were ours. We might be envious off those who got to go to Roy's but sorrowful rather than disdainful for the others.
A few boys had mothers or aunts who were hair stylists who would cut their hair. There were definite mixed feelings about that. They were often the boys who were allowed to have longer hair, and the girls certainly seemed impressed. We noticed that. But it also didn't seem very butch, in both the hair sense and the masculinity sense, to go to someone who usually cut girls' hair. There was a fear that they just wouldn't understand what was needed, wouldn't get it in some important sense and might give you a haircut that looked girly. Gulp. That you might get teased for. An ugly bowl cut was less shameful than an attractive one with even a hint of femininity. That was part of the deep suspicion of boy bands as well. Their hair was clearly styled, not done at Roy's or Stan's or Louie's.
I have little idea what barbershop culture is like now.