Dressed for Success? Or GNO?

When your smart friend makes inappropriate work clothes choices, how do you tell her it’s not Girl’s Night Out? Telling the empress she might be better off naked than hoochie.  — BadWitch

P.S. Happy Martin Luther King Day. Spread the Dream.

Readers Are Spellbound & Perplexed…

Dear GWBW — I met my best friend at our work. Sometimes she dresses like a hoochie mama. Or like she’s ready for the club more than a meeting. How do I tell her? I don’t want to hurt her feelings.  — What Not to Wear



Dear What Not to Wear,

It’s tough when your girlfriend thinks she’s amazing crazy, sexy, cool in the VIP lounge and the queen of the boardroom, too. Props for her confidence, but should someone’s self-esteem be tied to their sexuality, it can be an extra confusing line to tow. We know that no woman enjoys having anyone tell her she doesn’t look her best or most professional (and in certain environs, the line for appropriate women’s work apparel can be even thinner). Challenge! Be a BFF by telling your girl the truth but with the intention of helping her excel in the workplace by reinforcing the best of what makes her confident.

You know her personality best (and the healthy dosage of reality you can administer before she ODs and crashes), so keep that in mind while telling her something like this: “As your office BFF, you know how much I admire your skills and how smart you are here at work. But having gone clubbing with you, too, sometimes it seems to me that you confuse your two lives through your choice of work clothes. In the office I want your image to reflect your successful work, so I’m suggesting that you might consider clothes that people who aren’t your BFFs can recognize your smarts right away in. Maybe longer skirts and higher tops (fill-in-her-offenses), are more appropriate work clothes? The only reason I wanted to tell you this is so you can do something productive about it. I only ever have your best interest in mind.” Then drop it. If she is ready, she will take in what you suggest and enact her own spin on it, if not, she will probably still hear it subconsciously and file it away for later.

Smart friends speak up with love,



Dear What Not to Wear,

Much like telling a friend their mate is cheating on them, tread very carefully. If your friend is dressing like a “hootchie mama” obviously she draws a lot of her sense of self-worth from her sexiness. Asking her to tamp that down or letting her know you find it inappropriate, it may be taken as more of a personal slap than intended.

I find television to be very instructive. Style Network’s “How Do I look?” may be a great addition to your DVR cue. Then maybe a night with some wine, TV and well-placed comments. This show has friends tell friends when their “look” is inappropriate—either too trashy or, well, too trashy. The show even offers coaching for contestants, as well as makeovers, so you hear first-hand how to talk someone down off the Hootchie Mama Wagon.

Watch the show before-hand and decide whether you want to take your friend to dinner (definitely with wine) and discuss the issue of whether you want to do a covert, “Let’s watch some TV at my house. I saw the funniest new makeover show!” Perhaps check into some resources for personal shoppers and fashion consultants. Give your friend the opportunity to discover other sides about herself.

And lastly, somewhere in all this, let your friend know that she is a sexy, beautiful woman to the degree that flaunting her sexuality can create unnecessary competition, jealousies and unwanted attention. Let her know that you love and respect her. Let her know she’s sexy even wearing a garbage bag. Help her see her sexuality in more ways than a super short hemline and low cut blouse.

Be a friend. Tell the truth—one way or another.

Good luck,



Juicy Relationship Coaching for Leaders and Individuals.


Mondays money, work, purpose dilemmas. Thursdays family, relationships, love dramedy. Send your brewing questions on how to thrive—not just survive— modern life to: coaching@stillsitting.net.



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3 responses to “Dressed for Success? Or GNO?

  1. This is a good topic. I’d love to hear/read more in the future. Workplace styles have changed over the years. The business suit I wore in the past would be viewed as too old fashioned now. But what is appropriate office attire these days? (I’ll check the Style Network show you mentioned.)

  2. Nancy – Exactly and thanks! It’s also true that there is no One Size Fits All for successful dressing across industries, either. I when I worked with creatives and would visit my clients, I was invariably always the most “dressed up” in my jacket and jeans (!). Besides dressing appropriately (check your company’s dress code for clues, if you really don’t know what works or doesn’t for your employer), also be aware your roommate may be leaving far more casually dressed for her downtown job in a creative environ, than you might for your law firm one.

  3. Ya gotta let your pal know she ain’t working for Sterling, Cooper, Price and Draper. The whole hoochie mama thing at work simply does not cut it. The manner in which one chooses to dress at work does make an impression, regardless of what employers would like us to think. Take her shopping and gently suggest some more appropriate clothing. Maybe an accessory or two to tone down her look. Perhaps a business type jacket or sweater over her outfit, different color nylons, or lower heels would compliment her look rather than contribute to the “club” effect. Simple is best and does make a difference.

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