What people are reacting to isn't necessarily the specific item of clothing (though hoodies are ghetto, they're not GQ).
What they're reacting to is what your character is acting like. Specifically, your character is using skills and tools to actively put effort into concealing their identity.
In the ghetto that kind of behavior gets a different kind of reaction than in a world of professionals and privilege.
I do agree with Linekin on this one, you're making an attempt to disguise yourself from others around you. No matter what the ambient population is, in a city like Withmore that is known to have terrorist activity on Gold, etc you'd do well to be suspicious of anyone trying to remain unnoticed.
Branching out from that, I do remember a conversation way back when about more high-tech corpie like disguises including neck fitted hologram disguises, or the classic version of Total Recall alternative, maybe even a fashionable/trendy head worn product that covers your distinguishing facial features without making you look like an outcast among colleagues.
While having the latest in disguise technology might draw more attention once it's exposed it might just generate that much more RP in turn, which is never a bad thing.
At the very least the super rich... in theory ... should be able to pay for edgy, near-perfect prototype toy that has a good chance for critical failure. What's more CP than that? :)
I think all disguises should be technology based. Imagine a dynamic camouflage cloak that works but requires some type of training because if you move wrong using it - it doesn't work effectively, etc...or maybe even cyberskin with a limited time frame ala flashboost that requires you to be naked. Let's make it more CP people!
Fast movement produced an obvious blur that would be a perception check.
You still generate heat.
You need to not be wearing armor, etc making you vulnerable.
Any type of contact with water made the optic camouflage short out either entirely or intermittently
Also, i'm pretty sure this has been brought up both OOC and ICly at some point in the MOO but sounds like it never made the cut.