When It Comes to the Boss, Questions Abound

This article is from the archive of The New York Sun before the launch of its new website in 2022. The Sun has neither altered nor updated such articles but will seek to correct any errors, mis-categorizations or other problems introduced during transfer.

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This week we go straight to the letters as several readers sent in questions about dealing with the style and fashions of their bosses. It appears that many people’s view of the corner office involves not just the boss as a person, but the boss’s spouse, general taste and style, and eating habits.


Dear Jen:


My boss never irons his clothes and I think it would make a difference when he makes presentations. Is there a way I can suggest it without criticizing him?


– Dorothy, Baldwin, N.Y.


Dear Dorothy:


Actions speak louder than words. Bring in a steamer and just before a presentation tell him you are pressing your own shirt and jacket and will press his too since he would look so much better giving the presentation in a wrinkle-free jacket. Since you are doing it for yourself, you are eliminating any embarrassment and he will probably appreciate your thoughtfulness.


Dear Jen:


My boss is very fit and one of the lucky ones who can eat everything and never gain a pound. He is always snacking, lunching, or nibbling and loses his groove when I indicate the “none for me” signal. How can I continue to be an asset?


– Leslie, Livingston, N.J.


Dear Leslie:


This is a case of the old adage “if you can’t beat ’em, join ’em.” Bring your own stash of veggies to nibble on and break it out when he does. Let him know you want to be supportive during the planning sessions, but you also need to keep your figure or physique. Keep it light by reminding him you “need to look good” when you are out there representing the company.


Dear Jen:


I met my boss’s wife at an office party and was shocked at how outdated her dress and hairstyle were. We have been invited to their home and I want her to like me. I dress very high style and fear that she will interpret my fashion as trying to upstage her. Should I shift gears and tone down for the party? Any thoughts?


– Tiffany, Flushing, N.Y.


Dear Tiffany:


Dress classy but not flashy. Be yourself but, just like the office, be mindful of your environment and crowd. Find something stylish or pleasant about her and make a flattering comment. Let her know she has impressed you with table settings, food, or home decor, or her outfit for the evening.


Dear Jen:


My boss has asked me to go shopping with her because she likes my taste. The problem is her height and weight. The styles I wear won’t work for her, although she insists they will. How do I handle this and still be able to keep my job?


– Lenore, Princeton, N.J.


Dear Lenore:


Be truthful, yet tactful. I would look at this as an opportunity to bond with your boss by doing some research. There are some great plus-size lines that are very fashionable. When she steps out of the dressing room, remember “truthful, yet tactful.” Applaud if it is a winner, or give a thumbs down if the outfit doesn’t work. The less said the better as long as you are showing you are really into it and care. Remember, anyone with fashion sense has fashion sense for all sizes.


Dear Jen:


My boss is a slob and mocks me about my polished shoes and tailored suits. Sometimes he does this in front of customers. He is really smart about the business, but clearly is insecure in this area. Any suggestions?


– Christopher, Brooklyn, N.Y.


Dear Christopher:


You don’t have to say anything because he makes himself look bad every time. Even though he is being nasty, his mocking is bringing attention to something very positive and admired. Next time, click your heels together, brush your lapel, and smile!



Ms. Silano Foy is president of eFashion Solutions, LLC (on the Web at www.efashionsolutions.com) and has been a consultant in the fashion industry for more than 10 years. Send workplace or corporate fashion questions to styleforsuccess@aol.com.


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