In her memoir The Woman I Wanted To Be, Diane Von Furstenberg recounts the time in 1978 when she was on a flight from New York to Cleveland for a personal appearance to promote her iconic wrap dress. The plane was packed with businessmen and, except for herself and the flight attendants, there were few women passengers. That very morning, January 28th, the Wall Street Journal ran a front-page feature on Von Furstenberg and her fashion empire. Her seat mate spent the first few minutes of the flight ogling her legs. Finally, in an attempt to get a conversation going he said, “What’s a pretty girl like you doing reading the Wall Street Journal?”

Her anecdote reminded me about the time in the mid-80s when I was at my neighborhood bookstore (remember those?). I had stacked The Economist and Vogue on the counter and the male cashier said, “Wow, I’ve never seen the same person buy these together!”

This was before there were a lot of role models showing that women could be investors, wealth managers, and yes, even tycoons and that fashion and finance were not mutually exclusive. There was the unspoken belief that, if a woman was interested in money she was either a gold digger or kinda butch.

I encountered the same kind of sexist thinking—from women themselves— when I worked as the editor-in-chief of ELLE. When, after six months as a senior editor, I was offered the top job, I eagerly accepted and began to negotiate my new salary, benefits and perks. You know how women are always being told that the reason we don’t earn as much as men is because we don’t negotiate? (Is that really true or is that a convenient excuse for the sexism that’s baked into the corporate cake.) I negotiated on every point with my female publisher. And I was shut down on every, single one.

The kicker was she tried to make me feel ashamed of being focused on compensation, as though landing the editorship should have been reward enough. After all, this job was going to be so much fun that the pay should be secondary. I wonder if the same attitude applied to the guys who worked in marketing and advertising or the male fashion director?

It brings to mind a line of dialogue in the TV-series Boardwalk Empire. Margaret Thompson, wife of bootlegger Nucky, enters into a stock deal with Joe Kennedy (yes, that Kennedy). She tells him, Here’s an experiment for you: Think about the things you want in life. And then picture yourself in a dress.”

It’s fitting then that Diane, named for the Roman Goddess of the moon and the hunt, would create a business empire whose motto is: Feel Like A Woman, Wear A Dress. She leveraged a great name and juicy Rolodex into a multi-million-dollar lifestyle brand. She followed her impulses and made some killer deals. (Like buying property in the Meatpacking District when it was still pretty dodgy for $5 million and selling it a few years later for $20 million.) And, best of all, she did it wearing a dress.