In high school I refused to get a hair cut for years. Before leaving for college, I cut it shoulder length and shaggy. It was a common male style at the time. It's never really gotten longer than that.
When I got closer to transitioning, I cut it short. Last year before I came out, I started shaving it down with clippers. Now haircut day is a regular weekly event. I look forward to it, it's low maintenance, cost effective, and no one has said anything to me about it.