Though if I got in the habit of wearing a crazy costume and did other crazy stuff like leaving the house, all my hang-ups would work themselves out.
The first step is always the hardest, but after you take it, surprinsingly and for your joy, everything will fall into place.
I don't know if this happens to you, but I was always wondering what would people think of me in certain situations, for example talking on my phone in public (where everybody can hear what I say), or wearing a sight-seeker shirt or something along those lines. That really hold me down to do things. So I also figured, most people don't give a shit, and if they comment about it, 10 min later they would have already forgotten. And of top of that, chances are you'll never see them again in your lifetime. That helped me destroy these irrational thoughts I don't even know where the hell I got them on the first place.
What the heck, I was trying to google disapproving (spelling) and got disapproving cat. Is that a thing? Never mind, off topic.
My point, you're right.
But I have a ton of anxiety about doing or wearing something embarrassing in front of people I have to work with or talk to on a daily basis.
So, for the most part I keep my mouth shut unless spoken to, and just try to copy what other people wear. That way I'm mostly known as the quiet or shy person rather than the bizarre, awkward fellow. Inevitably I'll eventually acquire all of those labels if someone is around me enough, but at least I can make "quiet" outweigh "bizarre" nine times out of ten.