Performance evaluations are often more challenging for a small business owner than for a human resources manager at a large corporation. After all, you likely have daily contact with your employees and enjoy a familiar relationship. Talking about personal matters, such as dress code issues, in an evaluation can be uncomfortable, especially if you’re dealing with inappropriate attire. However, preparing in advance for the conversation can make it a positive conversation with good outcomes.

Prepare for the meeting. If you have a policy manual or employee handbook that outlines appropriate workplace attire, have a copy of it on hand to give the employee. While many small businesses have informal dress codes, having written requirements in place will make it easier to have a conversation about clothes.

Conduct the standard elements of your evaluation before addressing the business attire issue. Talk about goal meeting and performance issues and leave the discussion about dress code for the end of the conversation.

Make the discussion strictly about the business attire and not about the person’s judgment or character. Emphasize the fact that even though your company is small, your goal is to make a big impression, and the way employees dress is indicative of the professionalism of a business.

Focus on what should be done rather than what shouldn’t be done. For example, rather than tell a female employee not to wear miniskirts and tube tops to work, instead, issue a reminder about acceptable business attire and provide examples of what that entails, such as blouse and slacks, using your dress code policy as a reference.

Ask the employee if she has questions about appropriate business attire. Some staffers, particularly new hires or recent graduates, may not be well-versed in what constitutes professional dress. Serve in a mentoring capacity in addressing the issue and explain how the clothing people wear to work is a reflection of them and their positions.

Be prepared for an indignant or embarrassed response. Being told you don’t look professional in a work environment can be a blow to an employee, especially when the news is delivered by a manager or supervisor who will be seen every day.


Make sure your business clothing evaluation is based on something more than your own personal preference. Just because an employee is wearing something that is not to your taste does not mean it should be disallowed if it is otherwise appropriate for the business environment.

If addressing appropriate business attire one-on-one is uncomfortable, call a staff meeting and remind everyone of your dress code simultaneously. Even if it’s obvious who the office offender is, it will temper the remarks and make them feel less personal.