Sure you may no longer be the guy in cargo shorts and a T-shirt, but are you really dressing well?
One thing I experienced in my own style evolution, and continue to see from hundreds of men, is the conflation of dressing in a vintage suit (or other outfit) with dressing well.
We look to a recent time in history when men dressed better and choose to emulate their style.
It makes sense, but it doesn’t work because, at this point, dressing like you’re in the 1950’s or 60’s isn’t dressing well, it’s cosplay.
The only difference is your character of choice is a gentleman instead of a super hero.
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