Q: I have an employee who consistently pushes the boundaries of our professional dress code. Lately, it’s shifted from ‘too casual’ to ‘genuinely unprofessional.’ How do I address this?

A: If you have a good policy, ensure equal enforcement, and have legal awareness, then “handling” the employee becomes a simple, objective business conversation rather than an awkward, personal confrontation. Here is how I recommend navigating that conversation:

• Audit Your Policy First: Does your employee handbook clearly define your expectations? If your policy simply says “dress professionally,” you’ve left too much room for interpretation. Be specific about what is and isn’t allowed (e.g., “closed-toe shoes are required for safety” or “no clothing with offensive slogans”).
• The “Private & Prompt” Rule: Never address an appearance issue in front of the team. Pull the employee aside for a private, low-stakes conversation as soon as the trend starts. Waiting until you’re frustrated usually leads to a more confrontational tone.
• Focus on the “Why”: Avoid making it personal. Instead of saying, “I don’t like that shirt,” frame it around the business needs. Try: “Our dress code ensures we maintain a professional image that builds trust with our patients/clients. When you wear [specific item], it doesn’t align with the standards we’ve set for the business.”
• Watch for Legal Red Flags: Before you issue a formal reprimand, ensure the “violation” isn’t actually a protected expression. Under Title VII and the Americans with Disabilities Act (ADA), you may need to provide accommodations for:
  • Religious beliefs (e.g., head coverings or facial hair).
  • Disability-related needs (e.g., orthopedic sneakers or specific fabrics for skin conditions).
• Be Consistent: If you call out the receptionist for wearing leggings but let the office manager slide, you’re opening the door for a discrimination claim. The rules must apply to everyone equally.

The Bottom Line: A professional appearance policy is a tool to protect your brand and your team. When handled with a mix of directness and empathy, most employees are happy to course-correct once they understand the “why” behind the “what.”

For a sample script of an initial conversation to address an employee, click here.