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I've tried optimizing and making "my personal" wardrobe and so on, but found that I ended up with one or two favorites pieces and disliked the rest. It's like a MLB slugger who hits a homer once a week and strikes out the rest of the time. I've had more success with just finding a "style tribe" I like and dressing like that. It's more of an MLB "singles and doubles", a consistently good-enough approach. I think people who wear streetwear look cool, and I like hanging out with them so don't mind strangers associating me with them. Now I wear mild variations of typical streetwear and find it much easier and more effective. Mild variations because I'm in my 30's and am wearing young people clothes, so have to display a sort of "grey beard" attitude about it. It's easier, because I can just look at r/streetwear's wiki for ideas. And it's more effective. As far as walking around, it seems like people prefer the principle of minimum surprise. People can now look at me, easily slot me into "he's wearing streetwear", and they can then judge me positively, according to how well I'm being creative within that tribe. It's easier to say, "ah, he's doing the Lindy Hop and he's doing it well" than to say, "he's doing... Something... And I can't tell whether he's doing it well or not." There's also a satisfying coherence about it. My entire wardrobe is now singing the same song, no matter what I choose to wear that day. I could perhaps have found this coherence through my own idiosyncratic style, but it wasn't worth the effort.
The instant feedback concept works for low-tech measurement games too.
I like to guess the time then look at a clock to see if I was accurate. My hope is that it improves my sense of time, but even if it doesn't, it's a fun diversion.
And Shigeru Miyamoto (the Nintendo boss) says: "I've always enjoyed guessing the lengths of objects, which is why I carry a measuring tape around with me... For instance, I might guess that the table in front of us is about 1.2 metres long. Then I'd actually measure it with the measuring tape to check. If I got it right, I'd think: 'I'm on form today!' But if I missed the mark by a long way, I'd think: 'I've been slipping a bit recently!'"