I used to go to Southside barber and wait for about 30-45 minutes before I could get my haircut. It didn't matter if i went at 11 AM on a Monday, or 6 PM on a Friday. I always had to wait, and that got to be frustrating.
So I started researching and found a barbershop tucked away off of Shiloh st in Mt. Washington. Walked right in, got a great cut, had some good conversation all for a reasonable price. McGuinn's recently moved locations into a really nice new spot off of Murray Ave in Squirrel Hill. Aside from the haircut itself, the price ($20), the best part about McGuinn's is that you can make an online appointment. He blocks off 30 minutes for each haircut, so you don't feel like you're getting pushed and rushed out the door for the next cut.
Highly recommended barber!