I was on the fast track. It was just a little over a year since I was hired for an entry level position with a medical management company and I was promoted to executive status. I loved my job and got to travel and meet and work with wonderful people. I was good at managing others and excelled at my job.

Corporate headquarters was on Madison Avenue in New York City. We had just completed another three day meeting when I was summoned into the office of our SVP of Marketing. “I need to speak with you,”  she said. You need to change the way you dress. It is not appropriate.”

“What?” I replied. I had a closet full of Calvin Klein and Armani suits. “What do you mean inappropriate? I asked.

“You show too much cleavage and it’s not appropriate as an executive of this company.”

Well, others might have responded sheepishly that they would certainly address the issue.I just looked at her in disbelief. What was she saying? My attire was certainly not offensive. (Maybe in retrospect , it was to HER.) My suits were all attractive and professional. I had enough self-confidence to dismiss this conversation as “her issue”. Was she jealous? Was she insinuating that I was successful because I was using my sexuality? Not MY issue. I never changed one item of clothing to please her. I continued to dress to please myself and had a terrific few years at that company.

Fast forward a few years and I am at the pinnacle of my career. I am in Chicago at the corporate headquarters of a Fortune 500 company interviewing for CEO of one of their heathcare companies. I am wearing my power red suit. This was my final interview in a long drawn out interview process and I wanted to “close the deal”. A woman approached me as I was waiting for my interview and whispered, “Women don’t wear red here. It’s not appropriate.” What? Are we back with Nathaniel Hawthorne feeling the shame of the Scarlett Letter? Apparently so.

Well, I got the job despite the red suit but it has never ceased to amaze me how as women we are always walking a fine line when it comes to professional image and attire.

If we wear pants, we are choosing a more masculine appearance. Is this what is takes in some corporate cultures to succeed?

If we wear attractive feminine clothing, we are often called on the carpet for using our sexuality to advance our careers.

Should we wear high heels or not? Pants or skirts? Should our hemline be above or below the knee?

As women, have we made any progress in this area? Can’t we just be our authentic selves and wear what feels professional and comfortable?  After all, wasn’t Hilary Clinton chastised for wearing pant suits during the campaign? Was she judged on her attire more than her talent? And what does all the criticism of Michelle Obama’s wardrobe have to do with all her accomplishments?

Thank goodness for dress down days! Then we all get to wear jeans, no questions asked.