So you have an employee who’s outward appearance just isn’t quite appropriate for the workplace. Maybe he (she) is taking casual Fridays a little too casually. Perhaps he’s wearing clothes that are torn, wrinkled or dirty. It could be the multiple, creatively placed piercing’s or the message printed on the t-shirt. Whichever it is, he stands out – and not in a good way. You have to deal with it, but how do you do it without hurting someone’s feelings?

For starters, give your employees the benefit of the doubt. Chances are they’re quite unaware of their transgressions. After all, the rules are different in every workplace. Tight tops and short skirts might be appropriate in a trendy, fashion-forward environment, but completely out of place in the law office across the hall. Collarless t-shirts could be okay for a server in a neighbourhood pub, but not for a server in a downtown restaurant. And there are a great many people who simply don’t see their manner of dress as a priority. They don’t understand why it might matter.

The conversation isn’t easy, but it is necessary. The best approach is:

1. Pre-plan what you’re going to say and when. This is very personal territory, and you’re just asking for trouble if you try to wing it.

2. Start by acknowledging that you have an awkward subject to bring up.

3. Initially position it in terms of a benefit to them – e.g.: “Bob, I know how important doing a good job is to you, and I’m concerned that the unwashed clothes you’re wearing might send the wrong message to people – that you just don’t care”

4. Reinforce the company’s (or your) position – e.g.: “And our image is something that is very important”

5. Apologize for the awkward conversation, and reinforce their positive qualities – e.g.: “Bob, I’m really sorry about the awkward conversation. You do such a great job around here, and you’re a valuable member of the team…”

6. Ask for a commitment – e.g.: “Can I get you to be a little more diligent in the future?”

7. The next day, when the issue has been corrected, make a point to acknowledge it briefly and positively. Just a quick, quiet comment (“Nice shirt Bob!”) with an appreciative smile is all you need.

One note: If the issue extends beyond one or two people, it may be time for a written dress code for everyone to follow.

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