Pretty much that last paragraph of yours.

I don’t care if people see me as childish, weird,or even dumb. But that makes me hesitate for some reason.

May i ask what kind of clothes you mean?

Skirts, dresses, thigh highs, crop tops, and just generally the feminine section of the clothing store. So many items there that are a lot more interesting than what the mens section has to offer.

That reminds me of men's haircuts. If you're sticking to traditional short hair you basically just walk in and go... Okay, how much longer do I want the top than the sides and do I want a fade or a hard line? And that's pretty much it.

Going for longer hair as a guy just gives you so many more options.

I’m so annoyed by hair… I want to let mine grow so bad, but pollen allergies and long hair is an awful combination

It's definitely got a lot of caveats. For me, it is annoying to need to put my hair up every time I eat, otherwise I eat my hair. But I love the way it feels moving around and if you have any social anxiety it conceals your face when you look down, which can be helpful as an instant hideaway.

But yes, it is definitely many times less manageable than short hair. However... I don't have bedhead ever!