When I was a little kid, I didn't care what my hair looked like.
When I was in elementary school, my dad cut my hair himself, so we could save money. I'd sit on the stool in front of the mirror and he'd use this set of clippers to trim it. Except my dad has no idea of how to cut hair, and I would always end up with something that looked like he'd put a bowl over my head and trimmed around the edges.
And he wouldn't do it very often, so my hair would always look long and shaggy before I got a haircut; and then the haircut would look jarring and strange. So I got teased about it.
On the next-to-last day of 4th grade, my hair was growing down over my eyes, and I was very annoyed with it. I decided to do something about it; I got some scissors and went into the bathroom, and trimmed it a little. I could see better. What I'd actually done was to make a three-inch vertical square window through my bangs. Then I went back out, and got teased for the rest of the afternoon about my inverse-crenellated hairline.
That night, Mom screamed at me for cutting my hair. Then, Dad cut my hair. Next day, wearing another awful bowl haircut, more teasing.
In 5th grade, at one point Dad trimmed the hair on the back of my neck with the clippers, but still trimmed the rest of the hair with scissors. Teasing, when it happened; more teasing months later when, during a retrospective slideshow of the year's events, one frame had me standing facing away from the camera, bare neck and all. This was a little worse because I'd managed to attract the enmity of the class bully, who was a consistent enemy for most of that year.
I think my well-meaning 60s' liberal Vietnam-era intellectual parents also managed to make this worse for me. They would counsel me to avoid violence; avoid fighting; Star Trek had the same message. Some kid beats you up a bit, and they call the kid's parents.
Next time you see that kid, more beatings ensue.
By the time middle school arrived, I had managed to somehow convince them that the $8 they'd shell out for a haircut was worth the less-annoying existence it would buy me. Through most of high school I had an undistinguished mop of reddish-brown hair, until one day when we were going to the mall, and Mom said she was going to take me to the barber.
By this time, 11th grade, I had decided I wanted to grow my hair long, and I didn't want a haircut. Mom yelled, "It is convenient for ME to take you to the barber TODAY; SO YOU ARE GETTING A HAIRCUT TODAY!"
Having learned a little from my Vietnam-era parents myself, namely Nixon's Madman Theory, I decided I would show her that I should not be pushed, for the result might be extreme. I got her to bring along my friend Jason to the mall for moral support and I told him of my plan: to get a crew cut, an extreme change in appearance. And after they clipped it, Jason and I thought it was great; he said, "You look like some SKINHEAD WRESTLER named RAM."
The plan completely backfired moments later, when Mom saw me and said, "Oh, it's wonderful; you look just like Jim did when we got married!" (It turns out that crew cuts are pretty middle-of-the-road for Vietnam-era parents, who after all did grow up in the 50s. And this was the 80s, around the time Top Gun came out and made short hair momentarily fashionable).
Later on, in college, I managed to grow my hair nice and long. I had a ponytail, which started out as one of those little three-inch jobs that yuppie defense lawyers wear and ended up as an eight-inch long REAL ponytail. I had luscious locks that my girlfriends of the time liked very much.
When one particular grad-school girlfriend and I split up, I decided I wanted a change, partly as a way of saying goodbye to her whole alternative-religions natural-foods hippie Weltanschauung; and I got another crewcut. Not really a big change for me, but somewhat surprising to the other Buffalo folk, who'd never seen me with short hair.
That stayed for a while; throughout my subsequent jobs, and marriage, and divorce, and current Existence Period (see Independence Day by Richard Ford). Finally, thanks to some personal examples and a general feeling of personal transformation, I decided to go that one last step.
Reaction has been basically positive. Of course, as I pointed out to one complimenter, telling someone you don't think they look good with a shaved head isn't like saying you like their other Hawaiian shirt better -- they can't go back to the way things were very easily!
When we were in State College for the DCE/DFS Meeting we visited a place called The Saloon. It has this nice girl bartender (whose name sadly I didn't catch but she did give me candy). The bass player for the band had a shaved head. I caught his eye and said, "Hey, dude. Daily, or every two days?" He said, "Every two, unless I want to look good for work." He tossed his head, indicating the stage.
I said, "Yeah, usually after just one day there's not enough accumulation to make it worth shoveling again."

My 60s' liberal Vietnam-era intellectual parents.
And now I also look just like my dad.