I know there are rules about this in fashion. That it's best to juxtapose a vintage piece with something of today so it doesn't seem too costume-y.
But everyone loves to play dress up don't they? I remember getting my first Halloween make up kit with colors in a palette and prosthetic paste. I would pour over the guide to see the types of faces that were possible on mine: a cat face with whiskers, a warty witch, a pretty princess, a frowning clown.
I don't know why but I was particularly drawn to the clown face. Maybe because of it's liberal use of rainbow in the curly wig. It just looked so darned happy - a clown is the life of the party, even with a frowny face!
If the workplace won't let me pull off the ROY G. BIV ringlets, which I think they'd be OK with, maybe they'd let me takie client meetings with one of these chapeaus.
Every meeting needs a teddy bear once in awhile.