I have always cut my teen boys hair. I'm really good at it, and it's free so I have no advice. I'd say let your son decide. FWIW, at least here in America, there really aren't "barbers" much anymore. There are chain places that cater to men, but most are staffed by female stylists. My own stylist is a very straight, married with kids, dirt bike riding guy. And he's amazing. He doesn't have many male clients, though. At the end of the day, you just have to find someone who can cut your hair the way you like it. The setting doesn't matter. I cut my husband's hair weekly for 20 years until he decided to shave it due to thinning hair. He actually hated how barber shops would cut his hair. He preferred when I did it.