Reader Question, In Which I'm Told I Look Douchey In A Roundabout Way

Going back through some reader comments, I found this in response to "Red, Red Pants."

"Sorry and I mean no offense by this, but this outfit looks too douchy (sic) and too fratty. First ask yourself: would Marlon Brando, Steve McQueen, Sean Connery, or Cary Grant wear this? Would a 21-year-old in a fraternity wear this?"

As always, thanks for reading. I don't take any offense to your disagreeing with my taste, though  I submit that "douchey" isn't a particularly helpful adjective for constructive criticism. 

My response to your first question is that it doesn't matter whether or not these men would wear this outfit. Obviously all of these men were/are known, at least in part, for their wardrobes. It's smart to use them as a point of reference when building a wardrobe. Cary Grant is often fawned over by the menswear giant Alan Flusser, and Steve McQueen's clothes in the original Thomas Crowne Affair were splendid. That doesn't mean, however, that any deviation from what they wore is sartorial faux pas. None of the men you mention here were known to hold up their trousers using a tie instead of a belt, but you know who was? Fred Astaire.

Please bear in mind that I'm not saying that I'm on the same sartorial level as Fred Astaire (who happens to be my sartorial hero). I'm just saying that staying perfectly within the lines isn't always the best course of action.

I'll answer your second question with another question: Do you see a popped-collared polo shirt and backwards baseball cap anywhere in this photo?