I would personally not push for a 1-2-1 meeting with him but see how the band night goes and possibly mention getting together with him when you speak to him there- he might be free the next morning or surprise you by saying he was wanting to hang out alone later in the evening in any case (I really hope he does!).
I vote option 2 for dresses. Option 1 to me sounds like all out seduction gear and I guess the impression you want to give is sexy but relaxed (?)
