Leading by Example: Supporting Dress Code Culture

I recently had the pleasure of meeting with three different independent school leaders in three different Northern California locations. Each leader was incredibly accomplished, highly educated and very good at what they do. This diverse group included heads of schools, including one Rabbi, assistant heads of school, CFOs and directors of admissions, development and communications.

There was one common thread with each meeting and each leader—one that is remarkably different from their East Coast counterparts. Every leader was wearing the quintessential American classic blue jeans. No one was on Spring Break nor were these meetings on a weekend. These schools have adopted a simple, casual dress code.

Was I wearing jeans? No. In my business casual slacks, shirt and button-down sweater (Northern California was in a cold snap), I was dressed the way we do on the East Coast.

Yes, I am writing this from my Baltimore-area office wearing blue jeans. Certainly, the COVID-19 pandemic and the work-from-home shift have given way to a more laid-back, casual approach to professional attire. And, of course, the laid-back California vibe has always meant a more relaxed approach to business attire than we have on the East Coast.

So, what does a dress code have to do with school leadership?

It was clear to me that the school leaders I met in California have a great feel for their campus communities. Their attire reflects how their students dress. Is that a bad thing? Not at all. As I walked these campuses and saw the students (not in uniforms, for the most part), the visible connection between the students and the school leaders was clear.

On the East Coast and in other places across the country, more formal uniform dress codes—sport coats and ties, skirts or kilts—are still the norm. For some schools, traditional dress codes are a very important part of the on-campus culture. And the school leaders and other adults on campus dress in accordance to the dress code. It is an outward embrace of the school’s traditions and culture.

For me, the take-away is how the school mission—and leadership style—can be woven through all aspects of a school, including what the school community wears. The 1980s idea of “dressing for success”—it was certainly in my mind when I was a young, part-time Congressional staffer on Capitol Hill during college—still holds true today, though there is no longer a standard list of clothes and accessories that fit a rigid mold for success.

Think of it as “dressing for connection.” If, as a leader, your school has a more casual dress code, and you have a more formal style, perhaps consider a more casual approach. If your school has a more formal approach, consider how you can incorporate the school’s traditions and culture into a more formal attire.

A few examples that come to mind: There was a now-retired, longtime head of a Baltimore girls’ school who always wore the school’s color (red), a walking representation of school spirit. I also knew a division head, who followed the school dress code of shirt and tie but often matched his fun sock collection to what was happening with student life (school play, holidays, etc.) or even the lunch menu (Taco Tuesday, anyone?). It became a highly anticipated daily connection between him and his students.

Every leader and every school has a brand. How you dress sends a message not only about your school’s brand, but also about your personal brand. Dress with both intentionality and comfort in mind. That approach has always served me well.

President’s Notes
Jonathan Oleisky

Jonathan Oleisky

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