Annie Hall

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.”

My favorite of my riffs: During a careful combing of an Ohio thriftstore, I landed a black twill three-piece suit straight out of the 70s. Meaning: polyester. And TIGHT. It was garishly tight for the non-fashion, non-fit of the 90s, but I braved the public in it anyway. I loved the jacket’s wide lapel and playing with loosely knotted ties under the vest. I think I wore the whole suit twice, I got so overheated in it.

The white button-down shirt was almost an afterthought. Until recently, I’ve avoided classic collared shirts, unless you count the 90s flannels. I tend to wear tunics or blouses, and in my previous life in a not-so-swelteringly-hot climate I layered sweaters and blazers so much it didn’t matter what was underneath. Usually a worn-out rock t-shirt.

There was the issue of the button-down’s connection to preppiness. I disassociated from anything remotely preppy after the 8th grade (1984, the height of Preppy). It was too cautious, too prim, for me. In my years as a waiter I went through too many white shirts, bleaching, pressing and starching them daily. At one particular restaurant, the boss’s sister ran the floor during the afternoons and made it her business to inspect the cleanliness and neatness of her staff to nitpicking proportions. I was so paranoid that the uniform-police would get me that I gave up on all-cotton shirts because they wrinkled too quickly. Everything about white shirt screamed professional and conservative.

But I’ve been on a black and white kick lately. The only thing that looks good with those black tuxedo pants is the white shirt. And the best white shirt is the one that looks stolen, Diane Keaton-style. And who could forget the Roman Holiday version? I might need those bangles, too.

One more thing: I’ve started a new blog called Cloth Habit, devoted entirely to sewing! I’m blogging about sewing my way through classic pieces, starting with the white shirt; so if you’re interested in shirt-making details, take a lookee.