Ha ha! Nicely done. You are a woman after my own heart. Anyone who knows Stacy and Clinton is a friend of mine.
Anyway, as someone who also obsesses about this kind of thing, these are my thoughts: I think it's always better to be slightly overdressed and chic rather than underdressed. I also, however, hate looking like I "tried too hard". My personal happy medium: skirts. They are awesome, flattering, can be made casual or dressy with accessories and shoes (ballet flats vs heels) and also show a lot of character. The skirts out for fall are so pretty too, feminine and flowy.
I'm from the South and lived in the East for a while, and at least in the cities I've been (Dallas, New York) it seems everyone dresses up for everything. i'd think it's DEFINITELY better to dress up more than less. I personally would not wear jeans. If the get together is at some bar or super casual place, I would consider a pair of trouser-style or darker-wash jeans which (as you mentioned) are tailored, but I'd probably choose capris (if warm) or skinny leg trousers with boots over jeans just in case. Or dress up a casual pair of pants with heels and jewelry. And of course, the coat and shoes carry everything, regardless of what you wear.
Of course, I'm sure you know this but I wouldn't wear anything too risque, cleavage-baring, short, etc. etc....you never know where it might lead. (I'll bet the alcohol flows quite freely at these events, and beer goggles always seem to do more harm than good) Case in point = first episode of Grey's Anatomy
I better stop going on and on about this - I promise I'm really not terribly superficial! I just love clothes way too much for my own good, and am a tad bored at the moment, is all.
Maybe you can tell me how to dress out West, since I've never been there before and am hoping
to have interviews out there soon...