And, oh my, the clothes. That scene where Annie, dressed again after the tennis match where she meets Alvy, emerges in her loose khaki pants, man’s shirt, waistcoat that unbuttons to reveal a wide tie, her hat framing her face, her sisal tote bag slung over her shoulder — that is the scene that launched a million ill-advised teenaged girls’ attempts at men’s wear.

from Annie Hall and Shopping Menswear

I’ve never owned a bucket bag, but I’ve riffed on the rest of the Annie Hall look at various stages of my life. I was a wee child when the film came out but Annie was still cool in 1988, 1992, 1997, 2003. I could never relate to her nerve-wracking flightiness but I could to the carefully rumpled three-piece suit. It said (and says), “I’m almost too smart to touch down properly.”
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