In the summer I like short sleeve collared shirts, or polo shirts. In the winter I like long sleeve shirts. I don't really care for big slogans or logos. Maybe a discrete one on a polo shirt, but really only a tasteful, small one. I generally don't like shirts with big prints on them. I'm "old" though, and not the target consumer for pool clothing companies. If a middle aged man came into the pool hall in a hoodie with "grafitti style fonts" and some saying about being a hustler, I think most peoples reaction would be laughter. That notwithstanding, I see people pushing 50 whose pants are falling down when they bend over. I'd laugh if it wasn't so sad.
Most younger people play in hoodies and t-shirts, though. You can't really blame the manufacturers to cater to their customers. They want to be hustlers and gangsters, so that's what they make. Big garish logos, and "tough guy" expressions printed all over them. Every day on here hustlers, swindlers and all kinds of criminals are glorified and defended, even by the older posters. Hustlers are cool, apparently. Leauge and tournament players are "lame" and "sqaure", it seems.
Many pool players want to wear shorts, t-shirts and flip flops, because it's comfortable. Some are covered head to toe in tattoos. Of course when people not in the culture comes in, the entire pool halls clientele is dressed up- and inked like hardned criminals or homeless people. This isn't helped by the fact that this is not just a superficial first impression, but actually accurate for many of them. I certainly can understand why some pool room owners insist on dress codes.
That being said, it's best not to try to police others clothing. This is a sport that attract people on the fringe of society. I've made my peace with it. They'll wear what they want and I'll wear what I want.
However, I’m 59 so my opinion about fashion is useless. 
