Perspective | Have Insurance Professionals Misplaced Their Dress Code?
His father was an insurance salesman, but Jack Kerouac didn’t write much about insurance. His free-form writing in the 1950s chronicled the Beat Generation, the hip cats without whose louche influence you wouldn’t encounter many of the mannerisms you do today.
Back then, jazz musicians looked like insurers, e.g. Dave Brubeck’s sax man Paul Desmond. Now insurers look like jazz musicians. Well, not my insurer. His tie is his most important qualification, as far as I’m concerned.
Insurance men once wore ties. Now they wear whatever they like: jeans on a Friday, or a dressing gown when WFH. The whole system has gone to hell.
The other day, a friend’s son met us at a London restaurant frequented by senior insurance executives. The lad is 25, an underwriter with a growing company. His dad spent years with a major insurer, working above the actuarial level, a sort of one-man enigma machine of loss tables.
The youngster knew enough to wear a white shirt and a dark suit, like everyone else in the distinguished room. But his footwear was an Extinction Level Event: he wore brown shoes.
If a shiver ran down your spine when you read that, take a breath.
Obviously, he was the only man in the room, and probably the only man in London, wearing brown shoes that night or any other night.
Luckily, he kept his feet under the table all evening, or, like Kerouac’s fellow Beat poet Allen Ginsburg, I’d have seen the best minds of my generation destroyed by madness.
A gentleman wears brown shoes when, and only when, there will be mud.
I pointed out that the young man would present as a degenerate whenever he walked into a room. His father and I knew that he would never enter the highest offices in the industry in brown shoes. He’d be more welcome in prison stripes.
Yet my protestations were for nought. Youth must have its head, his dad said, and the lad was already on half a million dollars a year, so what did I know?
To dress for success is mandatory. I’ve offered style tips here before. For example, I described wearing a striped suit with a striped shirt and a striped tie as the trifecta of tomfoolery.
My editor tells me brown shoes are more commonly seen at insurance industry events these days. That doesn’t make them any more professional. (I did briefly sport a Gatsby-ish pair of brown spats. If asked, I would have said they were ironic, although no one asked. I see now that I was simply written off.)
My value also depreciated when I wore a repugnantly expensive silk polka dot tie on my first day at a stodgy company in Chicago. “What are you, a clown?” my manager asked.
I nipped out and bought the most ridiculously ill-tailored suit in history; two other people could have joined me in its voluminous folds.
When I wore it to work the next day, expecting ridicule, I was asked: “Are you interviewing with another company?”
Jack Kerouac rarely wore a tie. But you must, chaps, unless you’re writing an era-defining novel. &