The girls were three before they got their first haircut. Granted they are girls and I was in pretty much no hurry to get their hair cut. But it took three years to get to the point that we needed them cut.
For Jack... it was four months!
I figured I would try my hand at a home hair cut. The worst that happens is I would take him to a hair cuttery to get it "fixed"
We only had to trim up the "faux hawk" which made it super easy. It didn't turn out half as bad and I expected!