I'm not gonna profess myself to be the best dressed but after looking at too many "People of WalMart" photos, I've gotta be in the Top 20 of MY local WalMart.
Anywho, what the hell do you wear when a dress code is nebulous, say "dressy casual" or "creative holiday"?
Some would say that "one can never overdress" but I disagree. Instead, I opt to strive for the middle. Not the bland middle but neither overdressed nor under dressed.
Example, you're packing your bag to attend a national convention and will need attire for a cocktail party. What you pack is what you'll wear because there will be no time to shop. It's not your city and folks are coming from every state. What others consider cocktail wear may differ from your idea. Ladies who don't get out much will wear
Now, as I remember, the Preppy Handbook stated the best thing to wear to any event is the exactly the entirely inappropriate thing, like your tennis whites to a brunch party or dressy clothing to the PTA meeting because you have other places to go. What a great device to scoot out of a place you don't be!