Given the time of year, I'm a sucker for sun dresses, no-nonsense flats, brimmed hats, sunglasses and a mischievous smile.
At night, I like 2 kinds of girls: Ones in decent evening dresses (well fitted, doesn't have to be *too* revealing although I'm a sucker for a revealing back) tend to get the look, but I prefer girls in combat boots and miniskirts. There's gotta be some sort of attitude to her, though, and that's hard to quantify. Some girls can pull off "attitude" in burberry, others can do it at target.
Basically, Gwyneth Paltrow in the Royal Tenenbaums.