Best Dressed on Wallstreet?

We are talking about him.

I wish I had the courage to wear fancier clothes than I do.

Quality,well fitted clothing usually impresses me.

This guy doesnt look well dressed to me.

He stands out,but only in a garish fashion.

You would need to be an exceptionally handsome man to pull those outfits off without looking like you are trying too hard to be the 'zany' one in the group.

Each to their own.Sounds like it makes him happy.
 
It’s a form of peacocking, which helps differentiate himself from the crowd.
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