The Dress Code Puzzle

What are you going to wear today? Formal, business, casual? And does it really matter?

One thing that stood out for me over recent weeks are the “dress code” discussions I had at several events.

Something important is going on.

It started in Bangkok, where I was invited to speak at an artificial intelligence conference.

The event kicked off with a welcome dinner. It was Friday evening. The start of the weekend. The invitation didn’t mention a dress code, so smart casual it was.

Ooops. Many suits and formal dresses.

Should I go back to the hotel room and change? No. it’s just too warm in Bangkok. One minute later, I was in good shape. I spotted a speaker who was even less appropriately dressed than me.

He looked like he had just finished his sightseeing tour. He was still wearing his tourist outfit. Loud shirt and shorts and beach hat.

The next day (Saturday), the conference started. And again, it was a mix of outfits.

The tourist guy decided to change. He “over-compensated” and wore a formal suit and tie. I noticed him sweating uncomfortably for the rest of the day.

Two events. Two “bad” decisions.

Others chose to dress down — the result: lots of confusion.

Whereas in the past, everyone would have kept quiet about such sartorial blunders, people now discuss this issue openly. One participant even apologized for being the “worst dressed” speaker at the conference.

And it isn’t the first time that the dress code puzzle has been confusing and highly entertaining. It seems to happen more and more.

A decade ago, the expected dress code was clear and obvious. And, if you weren’t sure, it was always safer to take the formal approach and dress up.

The Solution?

One week later, I found a possible solution. Or rather, somebody explained to me what is actually going on.

I was invited to speak about “how every aspect of doing business is changing in the digital world.” A law firm organized the event for its business clients.

I arrived a bit early. The venue was an old courthouse — the perfect environment for an inspirational talk.

When I entered the building, I had a strong feeling of deja-vu (the welcome dinner in Bangkok): The lawyers — all of whom arrived early — were all dressed in formal attire.

I felt underdressed (jeans and a casual shirt). But, this time, I didn’t care too much.

And I was right.

When the clients arrived, it was clear that historical business standards are disappearing — jeans, t-shirts, sports coats, and khakis everywhere.

A mix of different approaches to fashion is slowly but surely becoming the new normal.

And this is the answer to the dress code puzzle.

After my talk, one of the clients came over to talk to me.

He pointed out how the young lawyer who had introduced me and thanked me at the end had looked very uncomfortable on stage in his formal suit. He seemed awkward and out of place.

And he knew it.

The client referred to my talk. Every aspect of business is changing, including the way we think about dress codes. And it isn’t about dressing down. It isn’t about replacing suits for hoodies. It isn’t about replacing one “uniform” for another.

Rather, we are moving to a world where you can just be yourself without pretending to be somebody else. It is more and more acceptable to wear what makes you feel comfortable. You can wear what makes you you.

It is a new world where identity, authenticity, and autonomy matter more than appearances. And the young lawyer up on stage with me knew this. He felt inauthentic in his suit and that was the source of his discomfort.

But We Aren’t There Yet

I decided to take the client’s message at heart last week. I had to give another talk to government officials and regulators. A formal dress code was expected, but again I went “jeans and a shirt.”

I stuck out like a sore thumb, but not in a negative sense.

My clothes helped me get my message across. I argued that we need more digitally savvy policymakers and regulators. All of them don’t need to become experts in artificial intelligence and the Internet of Things. But they do need to have an open mind about the changes that are happening all around us and they do need to listen. They must be able to think and act differently.

I heard afterwards that by wearing something “different” I had made the attendants think. They noticed my unconventional fashion taste. But it wasn’t criticized. I wasn’t chastised for being “underdressed,” but appreciated for being honest.

It made some of the participants realize that perhaps it is time to dare to think “out of the box.” The historical and traditional processes and procedures don’t work anymore in the digital world.

Of course, there are still many issues, but one thing I love about the digital transformation is the opportunity it gives to just be yourself. The “old rules” no longer apply. Everything is disrupted. And everyone can join in the project of defining the future.

The Startup

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Erik P.M. Vermeulen

Written by

What works and doesn’t work in a digital age? My take as a business & finance professor, a digital lawyer, restaurant owner, board member, and traveler.

The Startup

Medium's largest active publication, followed by +562K people. Follow to join our community.

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