Good one, Julia.

I think I'd have to go with that black sheath dress, hat, giant glasses, and little kitten heels she wore in Breakfast at Tiffany's (not the one she's most famous for, but the shorter "casual" version). Same hairstyle too.

Wow what a bunch of wonderful and creative answers. I had no idea this topic would be so much fun for everyone. I have to give props to Tanya for the idea because on another thread she linked a photo of her ideal outfit in some hypothetical situation.

My fantasy has me in the Mediterranean, with my husband. Strolling in a small beach side village. I'm wearing a strapless white bathingsuit top, bandeau style and a knee length (also white) flowing skirt. My accessories are a dramatic wide brimmed straw hat and strappy thong sandals. (Edit: and a big chunky pendant that magically does not create a tan line).

My husband is wearing , ah who cares what he's wearing--cuz everyone will be looking at me because I look so darn tootin' fabulous! All the tourists and a locals are sure that I must be someone famous!

Thanks for indulging me, everyone!

Thanks for the props Nicole! Very sweet of you, but I think that you deserve the credit for it.

Was this the post that you mentioned, this maxi DVF I said I'd die to wear on a (hypothetical) evening out on an exotic island vacation:
http://www.saksfifthavenue.com.....jcYVeGW0.w

Yep, that was it...