I've been going to see Tom at Golden Razor for the past four or five years after a long and fruitless search to find a decent place in Pittsburgh that won't leave me poor. He's not a stylist, so don't go looking for whatever you find in the latest GQ. He is, however, a damn good barber, so if you showed him a picture of what you wanted, I'm confident he could pull it off.
Tom's old school-- thick Italian accent. He's been at his Bloomfield location since '97 and before that, over 25 years in East Liberty (when the neighborhood was a sh*thole and not the resurgent place it now is). Tom remembers the regulars by name-- asks how you are, generally remembers what you've been up to, and asks how your family is doing. He does appointments alongside walk-ins. I've never left disappointed in a haircut and have money left over, even after a handsome (and well-deserved) tip. In sum, Tom's place is what a barber shop ought to be: plenty of magazines, great conversation and simple, inexpensive haircuts.
P.S. He's busy on Saturday mornings as one might expect. Schedule ahead of time, or enjoy the time just hanging out. Also, cash only.