Tomboy here in my late 20s. I wore dresses as a toddler by choice, but at some point in elementary school started feeling better in boys’ clothes. I wore only boys’ clothes for a long time, but then after losing my best friend to the popular clique, I felt a strong urge to fit in. I lost myself in girly clothes, never quite feeling right but ignoring it for years. It took having a crush on a woman for the first time to feel like I could finally let go and let me be myself; but I’m not gay. I’m bi, and the only representations I’ve seen of bi women are long-haired feminine types. I have way more success dating women than men.
I have to go to a special hair salon to get my hair cut the way I want it, masculine with just a bit of softness. I wear a mix of masculine and feminine clothing. I don’t think there’s space for me in the straight dating world. What I have found is that some straight men who are into masculine women cozy up to lesbians: if you’re a straight tomboy, you’re bound to find plenty of guys hanging around queer spaces. But as a bi tomboy, I don’t feel I fit into any category and as a result I’m just a category drifter. It used to bother me a lot, but nowadays I’m just focusing on other things and trying not to overinterpret my particular brand of bisexuality or tomboyness. Afterall, we all defy labels.