Should you tell a co-worker that she needs a makeover?

Question: “How do you tactfully tell a co-worker/friend, who recently received a promotion to an upper-level management position, that she needs to dress more professionally? She dressed very nice for the interviews, but the next day she was back to wearing wrinkled, sloppy clothing. She will be meeting potential donors and prominent business people, but she doesn’t seem to have a clue about her style. How can I help her succeed in her new position without hurting a friendship?” — Want to Help

What Not to Wear..? 🙂

Posted by: Liza | September 12, 2008 at 02:22 PM

If she’s truly a friend, then show your excitement about her promotion and ask when you can go with her shopping to expand her wardrobe. Say it in such a way that it’s just a “given” she’ll be buying a new wardrobe. Or, tell her that you’re updating your wardrobe since you feel that outside business activities are going to pick up and ask her to go with you! If she’s more of a coworker vs. a friend, keep your nose out of it and let her manager address the issue.

Posted by: Cindy Brock | September 12, 2008 at 02:23 PM

Does your company have a dress code? If so, you could gently remind her that she needs to meet the requirements. Since you called her a friend that might be the opening you need to take. If there is no dress code, then I would certainly go to her as a friend and let her know that she needs to dress for the position. Actually, you should dress for the next higher position if you have plans for upward movement.

Posted by: gamehen | September 12, 2008 at 02:24 PM

Stress the positive. If she is your friend she will value your comments. First tell her everything complimentary that you can find about her inside and out. Then tell her your concerns about her appearance just as you stated here. Then ask her open-ended questions. For Example, how you ever thought about having a makeover? Could you ever imagine how good it would feel to have a new wardrober, new hairdo, new makeup, shoes, etc.? Wouldn’t it be wonderful to have fresh, new looks every day? Have you ever thought about how easy it is to find a Mary Kay consultant at Do you realize facials and makeovers are complimentary? Have you ever thought about consulting with someone you trust to help you with a new professional look? Wouldn’t it be fun if we both did this together?

Posted by: Denise | September 12, 2008 at 02:28 PM

I was always told by my parents to “Dress for the position you want, not the position you have.” It has served me well.

Posted by: Anne | September 12, 2008 at 02:29 PM

I ran into this at a prior company. Since it was a very small company, the owner asked myself and another co-worker to take the dress-challenged worker shopping. He gave us a set amount to spend. We were able to take her shopping and let her try on ‘her’ type of clothes and then we would tell her why it wasn’t quite right and suggest other outfits. She ended up getting several pieces that worked together and she looked professional. I realize this wouldn’t work for most companies but it did work well for ours.

Posted by: Pam | September 12, 2008 at 02:33 PM

If she is a friend offer to go shopping in honor of her new position.
If she already has the clothing start by a meeting with anyone that meets with customers and remind them that they are representing the company. If you make comments (memos, emails, in meetings, etc) then you will be less apt to hurt this persons feelings. Remember that some people do not see clothing/ attire in the same eyes that you do. It might just be about educating them on how their clothing will make a better impression for the company.

Posted by: Bethe | September 12, 2008 at 02:45 PM

If she is a friend — easy. Congratulate, gush, and then tell her how wonderful she looked for her interviews, and remind her that she most likely sold an image that they probably expected to continue. Let her know that the people, who already know her, know how wonderful she is already, and want her to succeed. But the newcomers, important clients, etc. will judge her on first impression, so she should match her visual image with the position she worked so hard to get. The new responsibilities will probably be challenging enough, and you’re concerned that the first image she sends out may cast a shadow over her shining abilities before people give her an opportunity to sell her skills. Then suggest going shopping together to get her low-maintenance (washable/no iron), professional clothing fit for the position she now has and not the one she had.

Posted by: joyce | September 12, 2008 at 03:21 PM

I you are her friend I would just let her know that you noticed that the people in her position seem to be required to dress a little nicer because of their position, it may not be an actual policy but it is true what another suggested when you should dress the part you want to get. She may have just received a promotion but will her superiors feel she is committed to excelling in that position when she doesn’t even dress the part? She may cause herself to loose out on tasks and promotions in the future.

Posted by: | September 12, 2008 at 03:53 PM

Why not just come out and be straightforward about it? Mention that this position typically requires a stepped-up dress code, and that expectations are higher. Then, after being direct about it, volunteer to go through catalogs or window shopping to gauge what would be acceptable and what isn’t.

Posted by: Mark | September 14, 2008 at 03:56 PM

Mark, I agree 100%. This woman won’t learn anything unless somebody communicates openly with her about *exactly* what the issue is.

Posted by: Alison | September 15, 2008 at 01:44 PM

I have a co-worker that wears low cut blouses or camisoles that have lace. I’ve asked her before to cover up because it is disrespectful and distracting for other co-workers. I have been asked by a few male co-workers why she does this and I have no answer. The boss has even talked to her about this. Does anyone have comments about how to address this issue?

Posted by: Arlene | September 19, 2008 at 03:24 PM

If she doesn’t work for you, wouldn’t this be something her boss should address?

Posted by: Mom | September 19, 2008 at 03:27 PM

Hi. In your question you had said that she doesn’t have a clue about her style. I would disagree with that as she dressed nicely for the interview. She then “chose” to go back to her current way of dressing. I would approach it from that point of view. In other words, you need to keep the same “look” that you interviewed with as that was part of the decision when they hired you. Ask her if she thinks she would have gotten the job if she came dressed as she is today (assuming she is dressed down as you stated). That gets the thinking pointed the direction you want it to go and prevents any “finger pointing” on your part. Keeps it “real”. Good luck!

Posted by: Enola Bowers | September 19, 2008 at 03:49 PM

I am in the midwest. This matter can become an issue with ‘assertive’ personalities … if there is no ‘written’ dress code. This is where the maturity of the individual comes into high visibility. They can ‘dress’ to fit the ‘position’ or they will dress to fit their desire… not caring about the position. I believe the manager needs to take care of this – straight out.

Posted by: Becky | September 20, 2008 at 09:24 AM