My mother always told me, “Dress for the job above yours. No one will give you a promotion until they can imagine you in the higher position.” So when I worked at 31 Flavors in high school, I didn’t wear a baseball cap like the other scoopers. I wore a crinkly, white paper hat, with brown and pink polka-dots, because that’s what the manager wore.
For a while, what I should wear was clear. In college, when I wanted to be David Kramer’s girlfriend, I wore soft blue sweaters like his fiancé. At my first real job, I was “the Internet person” at a Fortune 500 company where everyone wore suits and I wore jeans because that’s what the guy who ran Netscape wore.
At some point, though, I got stuck. At some point between middle management and top management, I couldn’t find anyone to dress like. I rarely made deals with women and I rarely encountered a woman as I bounced between investors. When I did encounter a woman at my level, she wore a suit, or a least a jacket, which would not be appropriate at my own scrappy startup.
I wanted to wear clothes that would make me feel appropriate in a crowd of 20-year-old programmers and a crowd of 50-year-old venture capitalists. I noticed that khakis and a blue shirt do the job for men: The hip black shoes fit in with the programmers and the expensiveness of the shirt fits with the over-fifties. But khakis and a blue shirt on a woman screams, No style and probably boring — especially if she wears it as many days in a row as the men do. It’s a double-standard, but it persists, and probably-boring is not a trait people want in a leader.
So I hired a stylist. I hired one who dresses sets for sitcoms. But if someone’s sick she dresses the people. I tried to focus on the people instead of the props and that made me trust her. Her name was Allison. She looked at me as her big break into the high tech industry.
She took me to Nieman-Marcus and told me next time to dress nicer so we get better service. I tucked my T-shirt into my jeans. “Forget it,” she said. She said shoes are most important and my eight pairs of black loafers are not stylish. “Glamour is in,” she said, and she picked out shoes I would never choose.
I thought about the time the dentist told me about his business plan and when he took his fingers out of my mouth I told him ten companies already did that, and he didn’t believe me, and I thought he was a fool for not trusting an expert. So I tried to trust Allison.
The shoe salesman knew Allison was special. She knew the shoes he had in back. She knew the colors designers favored and said, “Don’t bother with brown from Chanel.”
I tried on Fantini heels and teetered. Allison said, “You look beautiful. Can you walk?”
I said no.
She said try.
She said, “You walk fine.”
I said, “There can’t be a hint of teeter because people already subconsciously think women aren’t sturdy enough to run a company.”
Allison sifted though shoes for lower heels.
The shoe salesman said, “But you don’t want the men to think you’re a prude.”
I looked at him. I looked for signs that he was scum. I don’t know what I was looking for. I was looking for a reason to scream at him. But he looked so young and innocent. Maybe this was his ice cream scooping job. I said, “Would you say that to a man who was buying shoes for work?”
He said, “A man would never buy heels.”
Allison looked up at me and gave me a sort of it’s-not-worth-it look.
But I persisted until he said, “You’re right,” in a way that meant, please buy shoes from me. He said, “I’m really sorry for offending you,” which meant, women are so volatile, I wish I were in the tie department.
I said, “Thank you,” which really meant, I am so gracious and you are ignorant and you will marry a woman with no self-esteem so that you do not have to notice your own shortcomings.
Allison hustled me through each department. She taught me rules of thumb: DKNY and Tahari are casual but sophisticated and that’s the look that lies between dinky startup and Fortune 500. I told the Mac makeup artist that I am a high-tech executive and I need to look a little older than I am. He told me to buy bright red lipstick and black-rimmed glasses. “Even if you can see,” he said. Allison concurred.
I unveiled my new look slowly at work. Lipstick one week. Glasses the next. Shoes on days I’d be sitting. I noticed as my wardrobe changed, the women who reported to me changed their wardrobes. Like my mom called them up or something. I tried not to think that Allison and I were making my office look like a sitcom.
Soon I started taking my appearance more seriously. And I ditched the glasses because I didn’t want any woman reporting to me to think she needed glasses even though she could already see.