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Who decides what "dress well" actually means?

My finger may not be on the pulse here, but I think we all deep down believe that a classic suit and tie is still dressing well... even if we choose not do it.

I despise suits in general, the pinnacle of boringness

Successful people, because other people imitate them.

Only in the Bay Area.

At least in NYC it is still fashionable to dress well (as in curating one's own style or to the upper-end styling haute couture well). If in NYC it is still fashionable, I am pretty sure it is still fashionable in a lot of places :)