To dress or not to dress—to dress up, to dress down, to dress to impress or to dress for success—that is the question, to savage the Bard, that leaders face every day. How should we attire ourselves?

The way we dress does matter—it can and will have an effect on our leadership. Mark Twain once quipped, “Clothes make the man,” but in a very different way, clothes make the leader.

When I was a young adult, I believed—truly, I wanted to believe—that others would make an assessment of my quality, characteristics, and skills based solely on my quality, characteristics, and skills. I’m probably not alone in this. I was not naïve enough to believe that some external factors wouldn’t come into play; I knew people would assess me in areas like height, attractiveness, and hygiene. But clothing? That seemed unreasonable—petty, shallow, and materialistic.

But one thing life has taught me is that, unfortunately but unavoidably, people do judge other people by the way they dress. Certain clothes in certain situations improve you; and certain other clothes in the same situation denigrate you. As a leader, making sure the right dust jacket is on the right book at the right time can feel like a necessary evil. But to paraphrase the Roman poet Juvenal, people won’t notice greatness under poor clothing.

One organization I worked at as a young adult had an “unspoken” dress code: golf shirts and khaki pants. At the time, I really hated khaki, and even more, conformity. So, I wore what I wanted to wear—let’s just call it very mildly “alternative” clothing. (No mohawks, nose rings or tats, mind you: We’re talking club shirts, jeans, and Doc Martens. Mild!)

Yet as mild as it seemed to me, what I wore was sometimes a subject of conversation—a slight running joke in my section of the office. I still don’t feel that what I wore affected my job performance. Or did it? Even if people under me seemed to appreciate my authenticity, did my attire undermine my standing with those in authority over me? Should I have dressed more like my superiors? To conform? To honor them? To fit in? To not stand out?

As a pastor for the last fifteen years, serving in small and large, rural and urban churches, I’d love to tell you that the way a person dresses is far, far less important than other, more “spiritual” issues. But if you’ve ever been to a church before—well, you know differently. Even in church, and certainly as a pastor, people always criticize and critique what others wear: too informal, too formal, too trendy, too boring, all the time. (Some may say: You’re at the wrong church! I hear you—but any church on this planet is a church filled with broken, sinful people who are going to struggle with judging a book by its cover. Let me be the first to confess.)

Whatever we wear never seems to “suit” everyone, at church or work or anywhere. So what can we say about our attire, leadership-speaking?

At this point in my life, I feel there are three keys:

First, as a leader, I assess the organization of which I am a part. What are the dress expectations (even if unstated and unwritten)? How do others dress? More importantly, what is the range of dress—formal to informal, boring to trendy—which defines the group?

Last year, my family and I moved to Europe for my post-doctoral sabbatical. While my relatives and friends thought I was crazy, I only allowed my family to take over two sets of clothes, budgeting enough to buy new (inexpensive) clothes there. The reason is that U.S. clothes are outside the norm there—if I wanted a hearing among scholars and pastors while I was there, my reasoning was that I wanted people to focus on me, not my strange, overly-colorful and non-European clothing.

Second, I assess my vision for my role in the organization. Is my job to connect with people where they are? Or is it to have a close tie-in with more senior leadership? Or is it to set the overall vision and direction for the organization?

In my present leadership context, I believe it is the last of those three, and therefore I dress so as to lead the organization in the way I think it needs to go. This doesn’t mean that I want people to dress like me, but that I want my attire to set the tone for the way the organization proceeds.

Third, I assess me. Know who you are, and then dress accordingly. What do I want to wear? Knowing my height, build, skin tone, and other factors of outward appearance, what should I wear for myself? (And if I don’t know that, where can I get help?) How compatible is what I want to wear with the context of the organization and the vision I have for my role in the organization?

At the end of the day, I still believe a person must be true to themselves in the way they dress. But a wise leader must weigh their organization’s context and their vision against their personal sense of attire, and dress accordingly.


One Response to Dressing Up Leadership

  1. zcochran88 says:

    I like how the man, Jack Daniels, who owned the distillery that has his name, always dressed in the same hat and jacket in public for the rest of his life since he was a teenager.