Boss Dresses Badly!

Question to Ask the Workplace Doctors about personal grooming: She wears clothes that are so old they are see through and wears an unsupportive unlined bra so we can see everything.

My boss dresses like she is still in the 80s. It looks like she rolls out of bed. Frizzy hair in a fabric scrunchy. She wears clothes that are so old they are see through and wears an unsupportive unlined bra so we can see everything. She is in a very high level position and it is embarrassing to be her employee. How can I delicately tell her about it?

Signed, Embarrassed

DearĀ Embarrassed:

I doubt there is any way you can delicately tell your boss that you feel embarrassed about her looks. But, you say she is at a very high level, so apparently she has been successful anyway. Maybe the highest levels in the company don’t mind–or are in the same boat you’re in about how to tell her she looks unprofessional, untidy and, with see-through clothing–embarrassing to others. Some people take the approach that as long as they are clean, nothing else matters. But, as you can attest, it is distracting to be around people who look far removed from the norm for a professional workplace. Even if she is a very nice person and very skillful, there is a point at which messiness becomes odd-appearing.

If you are a woman and know her well enough to do it, the next time she wears something that is very revealing, consider telling her in a confiding tone. “Sarah, I know you’d want me to tell you…I can see right through your knit top and your bra.” Or, “I hate to be the one to tell you this, but I know you’d want to know….something is showing!” If that doesn’t work and the revealing situations are bad enough to justify it, you may need to talk to HR or to the person above your boss about it. They may not want to say anything either. If they won’t, you may just have to accept her eccentricities and figure they don’t interfere with her abilities. If she treats you fairly and courteously, that is more than many bosses do. Please let us know what you try and how well it works. Your experiences will be helpful for others.

Tina Lewis Rowe

Tina Lewis Rowe

Tina had a thirty-three year career in law enforcement, serving with the Denver Police Department from 1969-1994 and was the Presidential United States Marshal for Colorado from 1994-2002. She provides training to law enforcement organizations and private sector groups and does conference presentations related to leadership, workplace communications and customized topics. Her style is inspirational with humor.