Robert Armstrong: Why does Jeff Bezos dress so badly?

It is a fait accompli, but still interesting, that the richest man in the world dresses terribly. Good clothes and fashion consultants can be bought for a little less than, say, a yacht so big that a historic bridge has to be dismantled before it can reach the sea. But Jeff Bezos, with a treasure bigger than Scrooge’s, has bad choices. What is the reason?

This is not to say that, for a modern multibillionaire, the clothing problem is an easy one to solve. For most – apart from the late André Leon Talley – a key aspect of dressing well is looking good without drawing too much attention to your own elegance. But if you have a billion dollars, everybody’s eyes are on you, all day. “Sprezzatura” [aparentar indiferença] it’s not an option.

That’s why many of the super-rich opt for simple uniforms: Elon Musk’s harmless dark suit and white shirt combo, for example. Warren Buffett understands. He manages to make his Zegna suits look like they came from Sears, and you can be sure this is part of the “I’m just capitalism’s good grandpa” trick he carefully perfected while earning enough money to buy Switzerland without funding.

Bezos doesn’t want to be anyone’s good grandpa, and he’s not content with a uniform. This was most evident last summer when he took a quick space tour aboard a giant flying vibrator. The blue flight suit wasn’t enough. He also wore a visibly shabby cowboy hat and boots (it is unknown who was tasked with putting the patina to use on these articles).

Fashion critics slammed on the brakes, anticipating a particularly horrible car accident. Jacob Bernstein of the New York Times coined the term “a Bezos” for any middle-aged man who has fallen deep into “dentist with a Lamborghini” territory. In GQ magazine, Eileen Carter found the model less pathetic than menacing, giving it a “general air of out-of-reach villainy”.

There are elements of truth in both interpretations, but I don’t think they solve the riddle (experts also didn’t notice the watch worn over the cuff of the flight suit, which may have been an astronaut thing, but felt like a vulgar parody of Gianni Agnelli). Perhaps it’s worth looking back a decade or two when Bezos opted for creased pants and baggy sports coats, and hadn’t traded the fuzz around his baldness for a fully shaved head. In photos from this previous incarnation, he looks kind, funny, and natural.

Something went wrong afterwards. One problem is that he got in shape and decided his outfit should enhance his muscles, starting with a tight fit. This has the opposite effect. As Daniel Craig has conclusively demonstrated in his James Bond films, muscle and tight clothing are a horrible combination. The combination radiates discomfort; all those poor drawn seams.

It’s a shame, because aside from the cut, Bezos’ taste in suits is very good. He chooses beautiful, textured fabrics. There are pictures of him in a classic turtleneck tuxedo looking almost dashing.

Problem is, he wants to highlight his work clothes when he should be running the other way. Huge tie knots are a specialty. He also bets on the tragic combination of jeans and blazer that, in rich and poor alike, tries to be informal but seems effortful.

The problem gets worse on “casual” Friday (as usual). There’s the notorious photo of Bezos in Sun Valley a few years ago, wearing a black vest over a black polo shirt that accentuated his biceps, along with aviator sunglasses – a sort of action hero outfit (Terminator: Dark Fate) .​

It’s a little unfair to poke fun at Bezos’ New Year’s Eve 2021 outfit: white Brunello Cucinelli jeans and a tight, colorful shirt, with prints that looked based on the tile floor of a particularly tacky Moroccan hotel. Her heart-shaped sunglasses make it clear that this is basically fancy dress. He’s having silly fun.

And that’s it. Bezos is a newly divorced geek with a lot of money. Does he not have the right to dress like one? What is the problem?

At the risk of being serious in a basically trivial context, I think there may, in fact, be a problem. Bezos is not just any rich guy. He controls a company that touches every part of American life. It employs 1.6 million people. There’s something about Bezos’ goofy and slightly crass style that clashes with the huge role his choices play in so many lives. Once again, in unexpected ways, clothes become important.