Originally Posted by Working Stiff
Clothes are a means of communicating with the people around you. There's nothing wrong with wearing a bowtie, or being the only guy wearing a pocket square, but it does send a message. If you are thinking about wearing these things, you should first be sure that that's a message you want to send.
Very well said.
There is often a difference in the way we wish
to be perceived and the way we actually are
perceived. I would take it slow and ask yourself whether a given wadrobe addition will draw negative attention.
Bowties, suspendered pants, double-breasted suits are going to raise eyebrows. I might work in a bow tie on a special occasion, for example. On the other hand, buttoning your suit (!), wearing a white pocket square in a TV-fold, or working in a nice pair of shoes will probably go (mostly) unnoticed. (No one needs to know your shoes cost $600, and anyway, sharing that information would be crass.)
Keep in mind that truly dressing well generally means not
drawing attention to one's appearance. We reserve that for the females of the species.