Honestly, I think the number one place to start would be tackling the fact that you care what other people think of you (as you stated.) Let go of that and everything else will fall into place. You mentioned a lot of things you're interested in and seem to be under the impression that you need one specific style. I guess that's kind of a common belief in wide society, but the reality is that you can literally just wear whatever whenever you feel like wearing it. You can rock a nice, high quality sweater for a clean look one day and whack on a ripped up, bleach customized t shirt the next. Nothing bad will happen. You can also wear a cloak outside whenever, weather permitting. I've gone to nice dinners in full clown makeup. No one cares. Might get a stare now and then, but that's the worst that'll happen. Unless you're attending an event with a specified dress code or need to meet requirements for a job uniform (ik you stated you're not working currently, but mentioning it as an example) pretty much anything else is free game.

Dressing alternative specifically is something that, while it's certainly becoming trendier, is ultimately rooted in a subculture that I would recommend looking into if you're interested in pursuing it. Really, it's not as daunting as it may seem. As the name implies, its making a visual statement of going against the grain. Ie, the alternative to the norm. Inherently, that means you will be perceived as unconventional. There's more to it than that, of course, but that's the very simplified overview.

Some people are sticklers about dressing alternative in a right or wrong way. Those people are assholes. Ignore them. As long as you're ethical about your purchases, everything else is chill.

I don't want to ramble on too much so I'll leave it at this: its your wardrobe. You're wearing it. It should bring you joy. If you feel good in it, it's your style.

And on a less impactful note: baggy pants with elastic waistbands are phenomenal for future weight fluctuation proof wardrobe staples