Ask a Boss: My Employee Dresses Like a Slob!

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Dear Boss,

We have a generally business-casual office. I have a direct report who just dresses sloppily. He is by the book following the dress code, but he kind of looks like he just rolled out of bed. He is clean, but looks messy.  He will wear a polo or Henley shirt, but rarely tucked in. Often his pant hems are frayed. He wears shoes that are the ambiguous type that are sneakers but meant to pass as shoes. The clothes are baggy.

We work in IT so none of the techs care too much about looking fashionable, but pull off a reasonably professional look with a simple polo and khakis and belt. This person’s role is supposed to be more forward facing and collaborative with others across the organization, not just sitting in a room coding.

I am also concerned that, depending on how I approach this, he will tell me that X is wearing the same thing as he is. However, X looks put together, not like he rolled out of a hammock in his office. I think that this guy would rather be sequestered in his office or work from home, but that is not the reality of the job right now. He is hurting his prospects with the organization as a whole because my boss views this even more negatively than I do.

I don’t want to offend my employee, who does do good work. Any suggestions on how to discuss this and get the point across to someone who seems clueless about clothing?

I used to work with a guy who we affectionately called “the unmade bed” because he was sloppy in a similar way. It was fine in his case — his work didn’t require him to look particularly polished. But in your employee’s case, it sounds like there’s an actual work reason for him to look more pulled together.

But if that won’t do it, then just be as straightforward as possible with him. People tend to agonize over conversations about dress and grooming because it feels so personal, but the more you keep in mind that it’s not about him as a person or a condemnation of his personal style choices, the easier it will be. The way he dresses is fine for his life; it’s just not appropriate for this job. That matters because if you go into the conversation thinking “ugh, you’re such a slob,” it’s likely to come out in the framing and tone you use. But if you go in thinking, “I want this guy to be noticed for his work rather than his frayed pants,” you’re more likely to sound like you’re on his side, which will give you both a better shot at an easy resolution.

It’ll also help to look at this like any other feedback conversation where you talk to him about something that you’d like to see change in his work — “here’s the issue, here’s what I need you to do differently to solve it.” For example, you could say: “Because your position works with so many other areas of the organization, it’s important that you look put together. When you leave your shirt untucked and wear sneakers and loose-fitting or wrinkled clothes, it doesn’t look pulled together enough for the visibility you have in this role. You don’t need to wear a suit; I’m just talking about fairly small tweaks.”

If you frame it that way, he shouldn’t be able to retort that a coworker is wearing the same thing. But if he does, you can simply explain whatever the difference is — that Bob’s shirts aren’t wrinkled, or they’re always neatly tucked in, or whatever the explanation is. And if relevant, you can also repeat that it’s his outward-facing role that makes the standards particularly relevant.

If he says that it’s unfair that he’s being judged on something other than his actual work, you can agree: “It is unfair. But the reality is that it will affect your credibility and I don’t want to see it take the focus off your work, which is excellent.”

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Ask a Boss: My Employee Dresses Like a Slob!