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If Will is widely recognized as being well dressed, then he by definition draws attention to his dress, does he not?
... dressing well as a middle finger raised in the face of the masses.
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For my part, there are days when on dressing up, I shake my head and mutter to myself, "I look so simple, even severe, that I could have arrived at my present station shortly after I embarked on my sartorial journey". But the truth remains, we all have to endure the entire spectrum. In other words, waste a lot of money (and time) to achieve the look like a court jester, then revert to simplicty - after much expense.
On the other hand, I think it's quite possible to err on the side of bland anonymity. Living in constant fear of attracting attention can be no better than seeking it out. Confidence, coupled with a bit of restraint, carries the day.