I first moved to Boston, and my gf at the time recommended it; luckily, my remaining hairs were in the hands of the Master himself, Tom. Ever since, I have sojourned to the South End every month-six weeks for Tom to take care of me. Great haircut, remembers your style (and your life), takes meticulous time with you, and it comes out looking fantastic every time (clearly dependent on what you started with). Super nice guy, lots of fun every time I'm in there, and can squeeze you in if you're persistent. Most importantly, he never disappoints, and that's why you're going there.
I have gone to a traditional barbershop all my life back in Michigan. I recently moved to Boston and I knew I had to find a good barbershop. After a few unsuccessful tries, I heard about State Street Barber. Their staff is professional, knowledgeable, and will work with you to give you a cut you will love. This placed has renewed my faith by mixing traditional atmosphere of a barber shop with more service than just using clippers. Well worth the money. .
This place is fantastic. I work at a local hotel and whenever a gentleman asks me for a place to have his hair trimmed, State Street is the only place I recommend. I moved to Boston about a year ago and have gone about a dozen times and each time is great. The people are friendly and they know how to cut hair. At first I was a little taken back by the price but when you can leave feeling good about the way you look, it is definitely worth it. Give Ben a try.