Interestingly, much of why clothing maps to wealth is precisely because of how much money someone is spending on the clothes. Buy a good quality piece, and you'll have it for DECADES. Buy "fast fashion" that looks trendy, and you'll be lucky to get a year out of it. So, in the long run, you're spending far more of your money on clothes. You're probably wasting your money in other ways, too, instead of investing it, like getting a car to impress instead of based on reliability and durability.

If you plan on wearing an outfit for decades, of course you choose something "timeless" and "classic". Although your point about tailoring stands -- in a study, people looked better in a $99 suit from Kmart that was expertly tailored, versus an $800 suit off the rack. Most people, when asked, thought the Kmart suit was more expensive, precisely because it fit better.