I really love the idea of #1...I like that's it's a little different, but I think it could be tough to pull off. I don't know if you have actally tried it on but I have found the fit of of lot of JCrew's summer stuff really unflattering. If you can pull it off, I say go for it! I think it could be fairly versatile.
I really like the second one. actually considered buying, but had no place to wear it. There's something off about the first one. Maybe the model is just standing funny, but I feel like the proportion between the skirt and the top is off, like maybe the top should be a little longer?
I love the first one best, but I have a question for you - you say only some will wear cocktail attire - does that mean others will be more casual or more dressy? If more dressy, than I'd probably vote #2. Otherwise, #1
Thanks girls, I ended up ordering the second. We don't have a J.Crew close to try them on so the more I thought about it the more I thought it was a safer bet.