Let’s Talk About Dress Codes and Clothes

What “dressing down” reveals about changes in how we live and work in a technology-driven society

“The digital transformation is clearly visible in this room.”

This was the opening statement of one of the speakers at a digital transformation event I attended recently. For effect, he paused as the audience looked around struggling to find who or what he was referring to.

“Nobody is wearing a suit.”

The response was interesting; awkward laughter as the audience couldn’t tell whether he was joking or not.

But, lately, I hear more and more such comments about the clothes we wear for work.

At an earlier event in Singapore, one of the speakers took a different view when asked about his decision to “dress down” and not wear a suit:

“This is just who I am.”

Again, this is a widespread view: “The clothes I choose to wear are an expression of my unique personality. This is me.”

Back at my digital transformation event, I stopped listening to the presentation and began to think about the meaning of clothes in a technology-driven world.

What — if anything — do changes in the workplace “dress codes” reveal about today’s world?

• Is this change a trivial issue that should be laughed at or dismissed; another (albeit small) chapter in the gradual expansion of personal freedom and choice; or
• Is this change the signal of a much broader cultural shift in a technology-driven society?

Of course, “dress codes” have always been evolving. And here, I am not referring to the many changes in fashion that I have seen over my lifetime. Recall the rapid decline in popularity of flared trousers in the late 70s or the David Bowie-inspired over-sized blazers of the mid-80s.

Instead, I am interested in workplace dress codes that both formally and informally define what can and can’t be worn “at work.”

More specifically, I am thinking about the shift from standardized and uniform dress codes to the more flexible approach that one finds in more and more companies today.

I have clearly experienced this change in my own working life.

When first I entered the corporate world more than twenty years ago, there was no question or discussion. Everybody had to wear formal clothing in the office. And, by formal attire, I mean a dark suit, dress shirt, and necktie for men. Women were similarly expected to wear a conservative formal suit and plain blouse.

This changed in the late nineties with the introduction of “Casual Friday.” The idea behind relaxing the dress code on Fridays was to stimulate interaction and engagement for at least one day a week in a more informal setting.

I still remember the first year it was introduced in my company.

Many people weren’t prepared for this new “responsibility.” Their wardrobe wasn’t built for Casual Fridays. The result? Confusion, anxiety and — often — highly inappropriate outfits that combined elements of formal suits and casual weekend clothing.

Over the last couple of decades, “business casual” has become the new normal in many companies. And wearing a suit in the office today merely results in questions or sarcastic comments.

A more traditional style is only necessary for particular places or events. But, recently, I notice that even this is changing.

I spoke at a FinTech event earlier this summer in which both bankers and coders participated, and the distinction was not between those in suits and those dressed casually, but those dressed in suits, those dressed in business casual, and those dressed in T-shirts or hoodies. It was still easy to distinguish the bankers from the coders, but the change in dress codes is real. That much seems obvious.

But what — if anything — does it mean?

A typical first reaction is to say that this change doesn’t mean anything. Changes in dress codes are dismissed as either unimportant or empty gestures, i.e., an attempt by a firm to project a youthful and more energetic corporate image. Senior corporate executives wearing black turtlenecks, in the belief that it makes them look like Steve Jobs, is an excellent example of such “window-dressing.” A purely cosmetic act that changes nothing.

We might easily conclude that there is no direct connection between innovation and creativity, on the one hand, and the way people dress, on the other.

However, as I looked around the room during the digital transformation presentation, I was not so sure that we should reject the importance of how we dress on how we think and behave.

I do think that this change has a broader and underappreciated significance.

Our clothes affect each of us very profoundly. They are an expression of who we are but, more than that, they also “trigger” specific reactions in us (and others) that open up (and close off) certain possibilities and choices. The clothes we wear give us the freedom and confidence to see and do certain things or, in other situations, not to see or do certain things.

Our clothes are a small, but essential, part of the “culture” that affects our behavior in organizations and other social settings. Another obvious example would be the impact of the environment. The layout of a building and the organization of rooms, for example, similarly affect how we think and behave.

The clothes that we wear and the spaces where we work are an integral part of the unique culture of an organization, community or other social groups. They play an essential role in defining how we see ourselves and how we see the world. They are an important source of action and interaction. And, as such, they do matter.

Let me offer a couple of examples.

When I attended corporate meetings in which everyone was wearing a suit and the room was organized with the senior person “at the front” the effect was very real: junior participants were inclined to keep quiet and respect the hierarchy. The formality and uniformity of the suit “triggered” formal and uniform behavior.The standardization of clothing functioned as a soft constraint on the willingness of participants to express a (contrary) view.

Of course, this didn’t always work. But, by and large, suits really were suits. They limited the choices that were available to us and kept us in our defined place.

Today, the introduction of choice has created the possibility of greater freedom and personal expression. In some ways, “dressing down” has been a liberation. When clothes don’t matter — at least, when they become nothing more than a personal choice — other possibilities are similarly opened up. Most obviously, expressing an opinion. But, more generally, a new degree of creativity and innovation is made possible.

So, whenever I see a brochure of a region that aspires to become the next Silicon Valley and the “leaders” of that regional ecosystem are all wearing formal clothes, my conclusion is simple. “Not going to happen.”

In the new world that is emerging around us, a premium is put on creativity and innovation. After all, this new world is all about openness, inclusivity, and flatter peer-to-peer transactions and interactions. In such a “best-idea-wins-culture,” the way we dress becomes much less relevant than before. It has become as irrelevant as your place in the hierarchy.

But this doesn’t mean that clothes don’t matter. I believe the speaker was right to say that the digital transformation was visible in the room. “Dressing down” has contributed and will continue to contribute to the disruption of hierarchies, standardization, and proceduralization.

The greater freedom that comes from the declining importance of what we are expected to wear has the potential to help trigger new freedom in other aspects of our work, and I am in no doubt that this change is a positive development.

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