I'm sure there are rich persons out there who shiver at the thought of (what they may perceive as) some low-income apartment trash wearing (thrifted) Tom Ford stuff, but then those same rich persons donate the stuff for tax purposes, thereby enabling the poor to wear such things, so...
In terms of overdressing, I couldn't care less. I, for one, don't care much for (very) casual clothes. I don't even wear polo shirts anymore (in fact, I'm considering never wearing half-sleeve anything again). I still have some jeans that see occasional use, but I'm phasing them out.
I keep thinking, what if I die today? I'd hate to be seen dead in a T-shirt/know such was the last thing I ever wore in life. :P
Then again, I'm autistic, so I don't think in the normal way.
I think "rich persons" is relative, but from my experience I think it would be more likely a pretentious, middle-class, nouveau-riche type who purposely wears certain clothes to appear higher status and separate themselves (God forbid somebody not recognize their status!) that was upset somebody "lesser" than them were wearing something they wear.
It's interesting that you say you're autistic. I was wondering if some of the folks on here so focused on clothing might be mildly so. The "shirt porn" type threads are particularly what made me wonder. But then again, I understand attention to detail. Further, it's interesting to think that somebody being autistic might lead them to overdressing or dressing inappropriately for a particular occasion. In regard to that, I agree with the at least one poster in this thread who said "part of style is dressing appropriately for the occasion."
Anyway, my last post hasn't showed up yet (must have not gotten through moderation yet), but personally, it's mainly wearing loafers with jeans that I'm concerned about. I don't want to do something that may somehow be inappropriate for me or deterrent to me socially. Generally, I am confident in my choices and believe that's apparent, so I'm afraid nobody would ever speak out if what I'm wearing is 'too much'.
I'm looking at a couple of pair of Allen Edmonds loafers that I like but can't decide between, but also a pair of Bass Weejuns from Macys. All 3 pair are penny loafers. The Bass Weejuns have souls that are black on the side, while the AE have wood grain. While I like the latter, the BW obviously would seem easier to step into when expanding my shoe horizons.
Here are the Bass:
And the two pair of Allen Edmonds:
http://www.allenedmonds.com/aeonline/producti_SF0994_1_40000000001_-1 (preferred color)
http://www.allenedmonds.com/aeonline/producti_SF0944_1_40000000001_-1 (potential other color)
Basically, I'm financially secure, doing fine, but have never worked in a corporate environment that at least requires an excuse to dress up. I dine out a fairly nice to nice places regularly, am travelling to Mexico again soon, enjoy wine, nice things in general, and am a pretty smart and educated guy. I did not graduate college. And I come from a hardcore working-class family who somehow or another I've ended up very different from. THEY scoff at a lot of my life choices and I know that it's just ignorance and lack of perspectice/education/exposure on their part, but still I think that might be at the root of why I question myself even though I *know what I like*. Surely somebody can understand how somebody cold be skiddish about transitioning into wearing nice shoes (and clothes).