My friend and I, we need your help

I'm tagging along with my friend Amy this weekend while she's in Nashville for work. It's mostly a girls' trip with the exception of a VIP, ahem, appointment that Amy has on Saturday night. With HSBF. Good luck figuring that one out. Anyway, we thought we'd solicit opinions.

Amy hasn't seen HSBF in quite some time. She needs to look hot, yet casual. Sophisticated, but not like she tried too hard. Flirty AND breezy but not standoffish.

So. We've narrowed it down. Should Amy wear look-at-my-butt jeans and heels? Or a check-out-those-legs (but just a peek!) skirt-and-casual-boots combo?

No shirt options.

Well, not because she doesn't intend to wear one, but because she's buying a new one*. Going shirtless would not be sophisticated.

And me? Oh, I think I'll get a pedicure Saturday night. Or maybe, if ME makes it to town, we'll go to dinner. Or maybe I'll hide in the bushes and spy on Amy and HSBF. Whatever, I'll have my cell on vibrate in case Amy should need an emergency exit. What are friends for?

Okay, vote to the right!

*If the shirt is found soon, I'll try to get some photos of Amy's options up on the blog. I can't be posting nekkid pictures of Amy though. Someone might report me for questionable content.