Enter the Era of Effort

Posted by Jack Donaldson on

The start of the year means that we’re currently being inundated with resolutions, good intentions and tips for living better lives in 2023. Personally, I’m not above a nice resolution. I would love to drop some pounds, read more novels, and ski the backcountry. Spend more time with my kids, be able to stretch down and touch my toes (something I’m not sure I’ve ever been able to do).

However, I’m also old enough now to be realistic about what I, or anyone else, can actually accomplish. Food is really good, time is really short, and interest rates are high. Maybe it’s enough just to try and not white knuckle all of 2023. Maybe it’s enough just to say, to quote The Mountain Goats, "I am going to make it through this year, if it kills me."

So I’m keeping most of my hopes for 2023 reasonable, but aspirational. And my main goal is the meat of this post. My goal is to see us as a nation finally push back against the downward spiral of Dressing Like A Slob, a scourge that has spread coast to coast for a decade or more. And I have to say, I’m optimistic about our chances.

I’m sure we’ve all seen the ills of which I speak. Gown men in sweat pants all hours of the work day. Shorts and sandals out to dinner. I was at a wedding with a ‘cocktail attire’ dress code where someone wore a Hawaiian shirt and jeans.

The thesis of the Age of the Slob is twofold. The first part may not be harmful, but it can be irritating. It is the attitude that instant comfort should reign supreme. The only priority should be the least amount of friction in what you wear. It is a sense that a lack of dress code also means an absence of decorum.

And the second part of this trend is more damaging. It’s the agreed upon idea that looking like a sack of shit is a signifier for genius, and not a signifier for insanity.

This last point is our nadir, I believe. It is truly a poisonous view, that a genius should present as a slovenly man-child, too occupied with matters of the mind to dress themselves appropriately.

Now, I live and work in LA, a city never known for it’s formality. It’s a casual place. I remember when I first moved out here from the East Coast, I was invited to a birthday party for a colleague out at a bar in West Hollywood. After work, I changed into what I thought was appropriate ‘bar clothes’ - OCBD, dark denim, brown shoes. I had come from New York where I had been turned away from certain bars for not having a collared shirt or for wearing sneakers. I had been trained not to take these chances.

I arrived at the bar and a fellow partygoer hit me with the cutting, “so, you didn’t get a chance to change after work?” It’s a land of T-Shirts and box fresh nike grails.

A film executive once told me that they expected screenwriters (male screenwriters. There’s still an entirely different expectation and coded style for women, as there is everywhere…) to actually look sloppy. If a writer had a ratty T-Shirt on in a meeting, unkempt hair, even shorts, it was a sign that he was so funny, so interesting, so clever that the idea of getting dressed wouldn’t even cross their mind. If a writer looked put together, the assumption was that the writer was just an aspiring executive and not a serious man of letters. If you want to be a writer and look put together, you better be a Sorkin-level talent or you look like a hack.

And of course it’s even worse up north in the Bay Area, where the tech mogul in sandals is aspirational for a generation of ambitious entrepreneurs and hucksters.

Sam Bankman-Fried is our rock bottom. The New York Times recently had an article about just this very thing, titled, “Hey Silicon Valley, Maybe It’s Time to Dress Up, Not Down.”

For a long time we didn’t even blink when a young man in child’s clothing would present a tech idea that could ‘change the world’ (eye roll), and VC firms would write them checks. With Bankman-Fried’s fall from grace and life behind bars seemingly imminent, it’s forced a reckoning.

Scott Galloway is quoted on the matter, and he makes the point that investors and others with deep pockets bought the Emperor-has-no-clothes vibe hook, line, and sinker. “The idea that a life of the boundless mind was reflected in a life freed from petty concerns like clothing.”

He goes on to say, “It’s the ultimate billionaire white boy tech flex: I’m so above convention. I’m so special I am not subject to the same rules and propriety as everyone else.”

And that’s the heart of the issue, isn’t it? Convention, rules, propriety. Taking a step back, do we really want to live in a culture that thinks all of those things are actually bad?

I am calling for the slow march back towards convention, propriety, and, yes, rules, when it comes to getting dressed.

I am not calling for a return of wearing suits and fedoras to work, like a Mad Men costume party or the early 2010’s when everyone bought tie bars.

This is not a universal endorsement of ‘formality’ or conformity. I’m not trying to be a ‘rules’ guy that says don’t wear brown in town, no white after labor day, or any other codes like that. And I actually have little quarrel with a Steve Jobs-style uniform of Issey Miyake and New Balance. More on that in a bit.

I am also not calling on men to suddenly start following fashion and trend reports. I’m endorsing style and intention, not trends.

Taken another way, all of this comes down to manners and respect. For yourself as much as for others.

Or, to paraphrase from the iconic contemporary philosopher Deion Sanders: “If you look good, you feel good, and if you feel good, you play good.” And if you play good, they pay good.

It can be easier - I mean, it’s obviously easier - to retreat to comfort and schlubbiness, because it shows zero effort. And effort is fucking scary. At my school the quickest way to get mocked was to get excited about something. Taking a hard stand for something, in this climate? Who knows how that’s gonna blow up in your face. So I understand the thinking that, if you look like shit, it’s not because you failed, it’s because you refused to try.

Roots of the decline of American style began in non-offensive ways; a sense of uniform, a la Jobs and Wozniak, that felt revolutionary but actually wasn’t so different from the grey flannel suit of decades past. A signature look is a worthy goal, and Jobs’ simplified dressing represented his view for Apple as a whole. Less buttons, less clutter - it works for an iPod and a sleek black turtleneck.

Zuckerberg, on some level, probably understood that to be the vanguard of a new generation of tech billionaires, he should follow Jobs’ lead and stay away from Brooks Brothers. He also found an advantage in playing to the ‘coding from the dorm room’ mystique that Boomers salivated for. Both of these guys had a level of ‘fuck you’ to their appearance that is as cool as Brando leaning against a motorcycle answering the question of, “what are you rebelling against?” with, “Whattaya got?”

[This will be the first and last time I will ever compare Mark Zuckerberg to Marlon Brando.]

But now we have guys wearing cargo shorts to meetings. T-Shirts with the collar stretched out. Socks that have lost their elastic. These things are worn without shame. This is not a considered style like Jobs, who probably chose Miyake as his turtleneck of choice intentionally, not because it was in the sale bin at Marshall's.

“Effortlessness” sounds cool. It actually sounds like the ideal a lot of us go for when getting dressed - the ‘lot of us’ that actually do care about how we look and care about the clothes we wear.

Effortlessness in this context harkens back to the 20th century titans of men’s style, like McQueen and Paul Newman, who looked at ease and natural in everything they wore. Who wants to look like a try hard? But, those guys actually did give a damn. Of course they did. They were men who got photographed for a living, who knew the right length of pant, the right depth on a V-neck, the right watch for the right occasion. Looking at ease with oneself is very different than looking like you give no effort.

Being opposed to effort is convenient because it risks nothing. But it’s a trap that leads to stifled ambition and less care for the world around you. And, frankly, without effort you lose out on joy and lasting love for people, places, and things. No one has ever had a successful love affair without effort, without risking something along the way.

So, here’s to a return to effort and care, which is really a return to love and joy. And who can be opposed to more love and joy in 2023?!

Are we still talking about clothes? Or something bigger? Sometimes it’s one and the same, baby!

Let’s take some small steps forward. Socks that stay up. Pants. Pants with a working fly and a button, for that matter. A collared shirt. Brick by brick, we can look better and maybe find we’ll be even more comfortable in our own skin that way. End the reign of schlubbiness, and enter the era of effort.

Who’s coming with me?!

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