Dressing the Part

I might as well face it. Bill Cunningham is never going to take my picture.

For the longest time I’d walk to work and as I neared the northeast corner of Fifth Avenue and 57th street, I’d smooth my jacket, square my shoulders, tug my pants hem out of the heel of my sneaker and hope that something, anything, in my colors or patterns would catch the eye of the octogenarian New York Times “On the Street” photographer.

Yeah … nah. I watch him scan the scrum at the corner where I’m waiting for the light. He sees me and his eyes register—nothing.

And I don’t blame him. I truly love fashion—women’s, men’s, high, low, movie costumes, opera gowns, whatever—from all eras and cultures. I love looking at it, reading about it, seeing it on actual people who know how to make it work. People who could come through a shipwreck looking crisp and clean, like Thelma Ritter in All About Eve managed their closets for them. But no matter how hard I try, within five minutes of donning something decent, stains bloom, buttons break, strings sprout . . . and don’t even get me started on the cat hair. If I try to iron, I put in more wrinkles than I take out.

Something about wearing anything other than jeans and sneakers just makes me feel squirrely.
And thankfully my bosses, even at old-school, non-dot-com publishing jobs, have had the sense to realize that as long as I do great work and show sartorial respect for important meetings, who cares how I dress in front of the paper clips?

When I was in junior high and listening to a lot of glam rock, I sewed a sequined snake down the thigh of my jeans, an homage to Alice Cooper. I even bought a pair of fat-soled, chunky-heeled, silver-glitter “marshmallow” oxfords that I had the nerve to wear maybe twice before a wiseguy classmate pointed out that I was using my shoes to compensate for my crippling shyness. Ouch. But he was right. And when I grew up, I learned that I liked “standing out” as a masthead name or an article byline, no glitter required.

I’m not going to lie to you; I’d be thrilled if Bill Cunningham ever found something in my ensemble picture-worthy. But the funny thing is, the photographer himself wears the same thing all the time: casual pants, black shoes and a bright blue French workman’s jacket (watch for him outside Louis Vuitton during the morning rush, you can’t miss him). He likes to work in clothes that make him comfortable. And so do I.

At right—what Bill was photographing the day I snapped him in action. Be sure to check out the wonderful 2010 documentary Bill Cunningham New York. And if you feel like sharing what you wear to work, please comment below!