What Should I Wear Today? The “Dress Codes” of a Digital World

A simple question but often difficult to answer.

Monday Evening. 11 PM. At home, I am thinking about tomorrow’s schedule. Teaching in the morning. A sales pitch in the afternoon. A board meeting in the evening. But what should I wear?

A decade ago, it was simple. There was a settled dress code of dark suit and white shirt. All choice was taken away, and the only decision I had to make was the color of my tie. A suit projected an image of sober authority. It conferred an identity that provided comfort and security. Colleagues and clients expected a suit, and it was convenient to meet those expectations. The costs of deviance were just too high. Clothes were a uniform. And, insofar as we followed that code, our clothes were invisible. Of course, they were important, but — ideally — we didn’t really notice them.

Tuesday Morning. 5:30 AM. My Apple Watch wakes me up. Wow. I feel tired. I look at the suit, the shirt and tie, and shoes. They don’t look inviting at all.

About three years ago, I was at an innovation conference in Singapore, wearing a suit. One of my co-panelists was wearing business casual. “Why are you not wearing a suit?” It was the first question from the audience. I will never forget his response. “This is what I always wear. I feel more comfortable in these clothes.” Of course, he was right. As the rest of us squirmed — hot and uncomfortable under the lights of an air-conditioned convention center — it was obvious. But I still thought it was important to conform to expectations.

Tuesday afternoon. 1 PM. In the car with one of my younger colleagues driving to the sales pitch. I discuss “dress codes” with him.

He agrees that the uniform idea is fading fast. He rarely wears a suit. Clothes still matter, but the expectations are no longer there. Wearing clothes to “belong” is much less critical. But what is striking is the speed of this change. It all changed in just a couple of years. These days you can wear a suit, a hoodie, or a t-shirt. “As long as they make you comfortable. And look good.” I feel better about my choice to leave the suit at home and go with a casual shirt, jeans, and trainers.

Tuesday evening. 7 PM. The evening board meeting. The discussion turns to the need for a more effective “digital strategy.”

I genuinely believe that a big part of Digital Culture is “individualization.” Individual freedom has become so much more important. Personal expression has replaced the twin comforts of uniformity and conformity. The need to stand out has replaced the fear of not belonging. Everyone must project a personal brand that reveals continuously to the world who they are and what they are doing. Social media has played a crucial role here in feeding this cultural shift by providing multiple platforms for projecting our individuality. Clothes still matter, but they matter in a different way. They show more about who a person is as an individual and less about the group to which they belong.

Tuesday night. 10 PM. Back home. It was a good day. I am watching a sci-fi show on Netflix and winding down.

I tell my wife about the clothes-themed day. She gives me that look. “Men should be careful when talking about clothes.”

Wednesday morning. 4 AM. Suddenly awake. A bad dream. AI has taken over the world, and I am a slave in a world of intelligent machines.

In science fiction novels and movies, uniformity often plays an important role. Everything is standardized in a dystopia. There is an image that in a world of super-AI and autonomous machines, value is found in uniformity and we — humans — will lose our individuality. Instead, the opposite seems to be happening and history is taking us in a different direction. We see more diversity and technology creates more opportunities to express our uniqueness. I don’t say that “individualization” is always a good thing. I do think it can lead to more creativity, entrepreneurship, and a “best-idea-wins-culture.” But it can also lead to more peer-pressure and pretending. What kind of personal expression is needed to attract attention, attract followers, likes, etc.?

Lying awake in bed, I remember something one of my colleagues, recently said. “If I wear a suit in the office, I feel like a grandfather. But nobody seems to care much anymore.” I think he is right. Everybody wears what they want. There are a few rules. But not so many. How we feel is all that matters. In a digital world, we still judge the appearance of others, but those judgments are less about conformity to a settled ideal and more about the quality and authenticity of an individual’s identity and actions. And, generally speaking, this cultural shift is to be welcomed.

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Video Gaming Prof • Middle-Aged Ultra Runner — on a self-learning journey

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