I wear whatever I want. I have a nice flashy bike and don't ride super fast, and only own one jersey and no real cycling shorts, so I'm sure there are some people out there who think I'm some sort of a poser or fred, but I don't care. I learned at a young age that it's a waste of time worrying about what strangers think.
As far as the saying hi thing goes, I agree with those that have said it depends on culture. When I lived in NYC strangers really didn't say hi to each other. Especially women. The traditional greeting for two NY women is the "New York Once-over" where they each assess whether the other woman is wearing "status-appropriate" attire and accessories. Dialogue is only involved if both parties "pass" the once-over. It's really very unnerving to the uninitiated. I doubt I ever passed a once-over. LOL!
Here in Minneapolis people say hi, which can be just as unnerving! For cyclists, I've noticed that the more serious-looking riders, when riding in my neighborhood, almost never say hi. In fact, they almost never even say "Passing on your left" as they practically take off your left shoulder. When I was riding in North Minneapolis, almost every other cyclist said hi to me. The first few might have thought bad of me for not responding, but it was so unexpected I didn't really get a chance to respond. I did say hello to a few, and then when heading back to my neighborhood I said hi to a guy I was passing and I think I scared him! So even in one city the culture can vary.
IMHO it doesn't matter if you say hi or not, or if the other person responds or not. It doesn't matter what you dress like or what other people think about it. If someone who doesn't know you is going to judge you on something so little or superficial as whether you said hi or if you're wearing the right top in the 5 seconds they saw you, they're probably not worth the effort you would put in to be friends with them anyway.



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