I Wore a Suit to Casual Friday

Last Friday I wore a full suit to a casual office environment. Jacket, tie, pocket square — the whole situation. And before you say anything, I want to explain myself.

I misread the email. That's it. That's the entire story.

Someone sent a "dress to impress" reminder and I thought that was about Friday. It was about the client meeting on Wednesday. Which I also attended. In jeans. So my record for that week was: jeans to the meeting that required a suit, suit to the day that required nothing.

The Problem With Being Overdressed

You become very visible.

People think you have somewhere important to be. They ask about the meeting. You have to explain there is no meeting, you just — you know — got dressed. It becomes a conversation. I had this conversation seven times before lunch.

By the afternoon, people were coming to find me specifically to ask about the outfit. I had become a destination.

The Pocket Square Situation

The pocket square was a mistake. Not aesthetically — it looked genuinely good — but functionally, because three different people asked me to justify its existence and I could not do it.

It's a small decorative cloth. It lives in a pocket. It does nothing. It contributes nothing to warmth, structure, or utility. It exists entirely to look intentional, which is, when you think about it, the most human thing in the world.

I still stand by it.

What Fashion Actually Is

Here's what I've figured out after years of getting it wrong: fashion isn't about looking good. It's about reading the room.

And I have never, not once in my life, successfully read a room.

I wore trainers to a black tie event. I showed up to a beach wedding in chinos and a blazer — overdressed for the sand, underdressed for the ceremony. I once wore a tuxedo on a first date because I thought it would be funny. It was not received as funny.

The suit was the latest in a long line of sincere miscalculations.

The Actual Rule

Wear what makes you feel good. Learn the context. When in doubt, ask someone who seems to know what they're doing — and actually listen to the answer instead of nodding and then doing whatever you were going to do anyway.

The suit was clean. The pocket square was excellent. The timing was catastrophically wrong.

Three out of four isn't bad.