Home › Blog

A FIELD GUIDE TO THE MAN IN THE SUIT JACKET AND TRAINERS He enters the meeting room at 09:

A FIELD GUIDE TO THE MAN IN THE SUIT JACKET AND TRAINERS

He enters the meeting room at 09:03. From the waist up: a man with a mortgage, a pension, and opinions on Q4. From the waist down: someone about to be asked to leave a Wetherspoons.

He is not one outfit. He is two outfits that met at a bus stop and decided to pool resources.

Let's be clear about what he thinks has happened. He thinks he has fused two worlds. Boardroom and basketball court. Davos and the Nike outlet. He has read that the founder of a company you've heard of dresses like this, and he has decided that the founder's £3bn and the founder's trainers are the same thing, and that by wearing the trainers he is now three-fifths of the way to the money.

He is not. He is a suit with a limp.

Look at the trousers. They have a full break. They were tailored — by a man in Norwich who is now dead — to sit on the polished toe of a black Oxford. They now hang, in confusion, over a shoe with an air pocket in it. The trouser doesn't know what happened. The trouser has questions. The trouser has, frankly, been through a lot since 2016 and this is the final humiliation.

Look at the jacket. Padded shoulders. Structured chest. A jacket built to make a man look like he could carry a coffin. Below it, a shoe built to make a man look like he's about to run from the coffin. The jacket and the shoe have not been introduced. They are communicating only through the trousers, and the trousers have stopped replying.

And the trainers themselves. Not the clean white minimal ones. God, no. These have a heritage. These have done a Parkrun. These have a small stain on the left toe that he tells himself is mud and that everyone else knows is the dog. There is a logo on them so large and so illuminated that in the video call it's the only thing with proper lighting.

He will describe this, if asked, as "smart casual".

It is not smart casual. Smart casual is a decision. This is a collision. This is what happens when a man puts on a suit, feels a twinge in his left heel, and thinks "you know what — nobody looks at feet". Everybody looks at feet. Feet are where the truth lives. You can lie with a jacket. You cannot lie with a trainer that's been through a puddle in Slough.

The saddest part? It's fixable in ninety seconds. A plain loafer. A derby. A shoe that says "I have arrived" instead of "I have arrived, but I may need to leave rapidly in the direction of a bouncy castle".

But he won't. Because the founder does it. Because the founder is worth £3bn. Because the founder, crucially, has a tailor, a stylist, and a pair of trainers that cost more than this man's car — and this man has a pair of Asics and a dream.

Dress codes are dead. Fine. But standards aren't, and neither is the trouser, though it has asked, in writing, to be.

Pick a half. Commit to it. Set the other half free.

The Probably Fine Daily

Threat intelligence every morning — new victims, new groups, what matters, in plain English. Free, with receipts.

Subscribe to the Daily →

View the original on LinkedIn ↗

← All writing