If a friend invites you to a restaurant chain and tells you to dress up, DO NOT wear the brand new Nannette Lepore dress you had overnighted specially for the Ferrari Christmas party and have yet to be photographed in. A much smarter route is a tee-shirt dress with a cardigan or shorts with a fancy blouse or sweater (even if you're going stag), not only do you look simple, aloof, and too cool to get all gussied up for a Friday night at Chili's (It wasn't chili's, BTW. I'd never ever go to chili's, even if the world was being eaten by giant tigers and the unbearable stench of the establishment warded off the attackers, making it the only place of human refuge. no, I'm not high right now.), and you give the other unfortunate single-for-a-reason girls a chance. well, not really.
Know that money can only take you so far, at one point looks have to take over.
you are never overdressed, everyone else is simply under dressed.
Confusing people (especially dumb people) in a crowded setting isn't that difficult, just spell a word wrong, switch some details around, or use a REALLY BIG WORD.