Dress for Success: My Mishaps with Fashion


The title of this column will surely convince my male readers that they were correct all along: any person calling herself a Crone is really and truly only writing for women.  But I would urge you to not judge so quickly.  If you are managing people you will probably have to manage a dress code, or lack thereof, at some point in time.  Even my young readers, safely toiling away in start-ups where dressing down is the norm, might face these issues some day.

Recently I was sweating away on my elliptical machine, watching reruns of  “Murder She Wrote” and realized with great embarrassment that at one time I owned three of the suits that Jessica Fletcher was wearing in this episode.  But admittedly I did come of age in an earlier era when businessmen wore suits and so did businesswomen.  I worked on Madison Avenue at a media company and we had a new President, recently reassigned by our corporate parent.  He was young, dynamic, said to be extremely smart and rumored to be a ruthless cost cutter under that charm.  My department head called us in to a meeting and warned us about him.  “He is seeking information,” we were told.  “Be careful how you answer his questions.  Give away nothing. Send him to me for more details. His goal is to turn this into a leaner, meaner organization.   If you talk too much, it will mean your job! ”  We scurried back to our cubicles, all terrified of being cornered and being the one to blather away, responsible for the downfall of the entire department.

Now, one of my good habits, even that early in my career, has been to get to the office early.  Very early.  And that was how I happened to get into the elevator alone with the new President at 7:30 in the morning.  He smiled and introduced himself.  He asked me what I did.  I was struggling to converse like a normal human being and not a terrified idiot.  I thought we would NEVER get to the 11th floor – my floor – even though no one else was in the building at that hour.  Finally the elevator dinged, the doors opened, I smiled, said it was nice meeting him and stepped out.

My stiletto heel caught in the gap between the elevator and the floor and I did a face plant with my skirt over my head in front of the new President.  He jumped out, helped me up, asked me if I was ok and then said, “Kathi, I am so glad I got a chance to know you better.”

While there were other fashion mistakes as my career grew and developed, none were quite as humiliating.  There was the time an assistant told me I was a “vision in cranberry” but perhaps the monochromatic look was better suited to another shade.  Or the sales conference during which the hotel’s head of group sales brought my assistant the complimentary bottle of champagne, not surprising since she was the one wearing the fox coat and had the matching Louis Vuitton luggage and I was wearing an army jacket and carrying a duffle bag.  As my responsibilities grew and I was required to travel more often, I developed the NYC businesswoman’s basic black wardrobe – everything I owned was black and I learned to accessorize with jewelry and scarves.  I could go to Europe for 10 days with a carry-on bag!

With greater responsibilities and larger staff it became quite clear to me that the men who reported to me rarely had fashion mishaps.  In more formal settings they wore suits and usually the worse thing they did was have bad taste in ties, or no sense of style, choosing a cut that was unflattering.  In less formal settings, the men wore khakis and a button-down or a polo shirt.  Loafers.  On really casual days, maybe the guys wore jeans.  But their clothes were in the background and that was a good thing.

It was a different story for some of my female employees. I emphasize it was only some, but the drama of the stories more than made up for the relatively small number of fashion faux pas.  We had our standard see-through tops and way too short skirts and flip-flops as footwear.  But my leadership ability was questioned right after our new German owners acquired our company and the Management Board member who was my boss had come to visit and meet and greet his new employees.  At the time, leggings were all the rage and some of our female staff members had taken to wearing leggings with long tops.  As executive W.  made the rounds, shaking people’s hands and smiling, I noticed a look of confusion pass over his face.  He turned to me and whispered,  “Kathi, these women wear no pants!  What kind of place do you run here?”

As a feminist, I find a discussion about dressing for the office complicated.  Very recently, Emily Peck, Exec. Editor of Business and Technology for The Huffington Post led an article with the line, ” The rules for dressing for the office are completely different for men and women.”  Peck went on to talk about Sheryl Sandburg dressing as the adult at Facebook while Zuckerberg gets away with wearing jeans, a t-shirt and hoodie.  The standards for women are different.  Yes, I do think the conversation should focus on capability and performance and yet whom am I kidding?  How we look matters.  It seems that there are more ways for women to get it wrong and subtly contribute to not being viewed in the best possible light.


“The difference between a man of sense and a fop is that the fop values himself upon his dress; and the man of sense laughs at it, at the same time he knows he must not neglect it.”

Lord Chesterfield



Join the discussion 2 Comments

  • Loved this post – and they way it acknowledges that attire/grooming matter. Unfortunately, more so for women than men. Hopefully one day that will change. But more than 400 years ago Shakespeare wrote” “Costly thy habit as thy purse will allow, for apparel oft proclaims the man.” Or – something like that! Still true today not matter how much styles have changed! Thanks, Kathi!

  • Jennifer Bender says:

    Excellent post – hilarious and very true.

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