A picture of me before I had long hair
When I grew up, I always felt like I was different than the other guys I hung around, certainly not as different as someone who's gay or trans might feel, but enough so that I've often questioned whether I am gay or trans. The way I'd describe myself is male, but with a tendency to value that which is considered feminine over that which is considered masculine. The media I like also seems to reflect this: my favorite TV show is My Little Pony: Friendship is Magic; I'm also quite fond of the original Powerpuff Girls and the newer Star vs. The Forces of Evil. Put this all together, and you have me watching My Little Pony: Equestria Girls one day, observing the very long and expressive hair styles of the main characters, and thinking, "Why can't I have amazing, beautiful, super expressive long hair like that? Why do I have to have boring, short, generic hair?" After that thought, I resolved to try out long hair, and after that year's marching band seasons was over (for marching season, it's easiest to have short hair) my hair was never cut short again.
How I looked with slightly longer hair during freshman year of college
Of course, just because you're not cutting your hair shorter doesn't mean it becomes long instantly. My hair remained mostly short throughout the rest of high school, and by the time I started college, it was longer than I'd ever had before, but by no means long. Only near the end of my freshman year did I start running into the "my hair keeps getting in my face" problem, and I started thinking about what to do with my hair now that it was longer. One day, I had just finished doing my laundry and was fiddling around with a few hair ties when I tried putting my hair in pigtails. I looked in the mirror, and started laughing at how cute I looked. Once again, a thought similar to the one about long hair came to mind: "Why can't I have hair that's cute like this?" The answer to that question is "because you're a guy" to which my mind retorted "that's a pretty lame reason" and thus, I started putting my hair in pigtails, and it became the default way I wear my hair.
The selfie I took when I tried the pigtail look for the first time.
In the two years I've worn pigtails, I have gotten almost no crap from anyone about it. For the most part, people don't care or they don't comment; occasionally an acquaintance asks why I have pigtails (to which I still don't have much of an answer besides "I like it"), but 90% of the time someone does make a comment, it's usually a "I like your hair." I've never had anyone compliment me on my hair before I got pigtails, yet alone complete strangers. Other perks of the hairstyle include being instantly recognizable, since very few guys rock the pigtail style (personally, I've never met another), making pigtails the best hair choice I've ever made. So as long as I like the look, I'll be wearing my hair in pigtails, though who knows what I'll decide I like most when my hair grows even longer.
A more recent picture of me with my pigtails, growing longer and longer.