Summertime! Managing Workplace Dress Code

The Reality Check

Picture this: Your COO can't stand the sound of flip-flops in the hallway, but your star employee—a single mom doing excellent work—wears them daily because they're what she can afford.

No formal policy exists. What do you do?

This scenario plays out in offices everywhere, especially as teams return from remote work. The key isn't having perfect policies—it's knowing how to navigate these conversations with empathy and clarity.

Start With Yourself: Two Critical Questions

Before addressing any dress code issue, ask yourself:

1. Is this my personal preference, or does it truly impact our work? If it's just your preference, consider whether it's worth the conversation. If it genuinely affects client relationships, safety, or team dynamics, then it's worth addressing.

2. Do we have clear, written policies? Unspoken expectations create confusion and resentment. If standards matter to your organization, document them clearly, and make sure everyone is trained on them.

The Framework: Leading With Curiosity

When dress code conversations are needed, use this approach:

1. Create a Safe Space

  • Have the conversation privately, never publicly.

  • Schedule dedicated time rather than catching someone off-guard.

  • Frame it as support, not criticism.

2. Lead with Curiosity

Instead of: "Your outfit is inappropriate." 

Try: "I wanted to check in about our office dress expectations. Help me understand your perspective."

This opens dialogue and may reveal context you hadn't considered—financial constraints, cultural differences, a misunderstanding of policy, or other challenges.

3. Focus on Shared Goals

Connect dress expectations to business needs: "Our dress standards help maintain client confidence and support our professional environment. Let's work together to make sure you feel comfortable while meeting these needs."

4. Collaborate on Solutions

Ask questions like:

  • "What obstacles are you facing with our dress expectations?"

  • "How can we work together to address this?"

  • "What support would be helpful?"

Common Dress Code Challenges

Most violations stem from:

  • Unclear or outdated policies.

  • Financial constraints.

  • Body changes (common during the pandemic).

  • Cultural or generational differences.

  • Confusion about hybrid work expectations.

  • Testing boundaries rather than intentional disrespect.

Practical Strategies

Update Your Policies

  • Refresh dress codes to reflect current workplace realities.

  • Define expectations for different situations (client meetings, regular office days, video calls, etc.)

  • Explain the "why" behind standards to build understanding.

Address Issues Early

  • Discuss dress code policies in interviews so candidates are clear on expectations.

  • Include dress expectations in return-to-office communications.

  • Have regular check-ins rather than waiting for problems to escalate.

  • Approach violations with curiosity, not criticism.

Consider Practical Solutions

  • Flexible dress-down days

  • Company-provided logo wear

  • Phased implementation of stricter standards

Stay Consistent but Contextual

  • Apply standards fairly across similar roles.

  • Recognize that different positions may warrant different approaches.

  • Maintain equity while acknowledging individual circumstances.

Sample Conversation Framework

Opening: "I'd like to discuss our dress code expectations to make sure you have what you need to feel confident and successful here."

Share Facts: "Our policy requires [specific items] for [specific situations]. I noticed [specific observation]."

Show Curiosity: "Help me understand your perspective. Are there challenges I should know about?"

Collaborate: "What would help you feel comfortable with our expectations going forward?"

Set Clear Expectations: "Moving forward, I need to see [specific requirements]. Does that feel manageable?"

Offer Support: "What questions do you have? How can I support you?"

When Emotions Run High

If the conversation becomes tense:

  • Pause and breathe.

  • Listen for underlying concerns (fear, embarrassment, frustration).

  • Acknowledge their feelings: "I can see this is uncomfortable for you".

  • Refocus on facts and future expectations.

  • Seek mutual understanding.

The Bottom Line

Effective dress code management balances professional standards with human realities. The goal isn't perfect compliance—it's creating clear expectations while supporting your team's success. When you approach these conversations with curiosity and empathy, you build trust while maintaining the standards your organization needs.

Remember: Trust is built one conversation at a time. Handle dress code discussions thoughtfully, and they become opportunities to strengthen relationships rather than damage them.

Beth Wonson