During the holiday season, it's very tempting to put on your best attire and deck yourself out for whatever holly-bedecked event has come your way.
For example: This young man, whose name is Justin Bieber, is appearing tonight on CBS's A Home For The Holidays With Martina McBride, where he has decided to wear his very best red pants, denim jacket, and fedora. This is a bit like wearing a clown suit with a cummerbund, unfortunately. The fedora says, "Welcome to the Starlight Lounge." Everything else says, "I got a C-minus. My mom is going to kill me."
The fedora [or, as has been pointed out to me, other smart hat], properly deployed, says cool. It says suave. It says look at me, I'm emotionally unavailable, but in a good way.
Unfortunately, the smart hat is too often deployed to say look at me, I didn't have time to wash my shirt, but that doesn't mean I'm not pretty much the guy "Puttin' On The Ritz" is about.
So how can you tell if your hat is a good idea? Imagine someone you love — your sister, brother, best friend. And think, "If someone wearing this particular hat in the manner that I am wearing it were to make a romantic advance to this someone I love, would I conclude that there was a jackpot to be had, or would I conclude that questionable forces of possible jerkitude had invaded and needed repelling?
As a general matter, the smart hat will work as long as it is one element of being dressed up. You don't actually have to be from decades past. When you're still communicating that you deeply, truly care about your coolness and your hotness simultaneously, you can find success.