I don’t consider myself to be an especially stylish person—or a slob. I dress somewhere in the middle. I am not the most rakish man at the wedding, but at least I’m better than your Uncle Brian, wearing his Jimmy Buffett It’s Five O’Clock Somewhere T-shirt in church. I do not resemble one of those gentlemen you see in magazines, effortlessly pulling off a three-piece suit, a bespoke shirt rakishly unbuttoned past the second button, a leather monk-strapped shoe placed atop a luggage trunk—not a bag but a trunk, suitable for a transatlantic voyage. I do not look like that. I look like a guy who put on his nice shirt to go to the dentist. I do not dress up for the train, my birthday, or the movies, and when my wife tells me to put on a sweater for the holiday cocktail at her dad’s, I kick an imaginary aluminum can. I wear shorts in October, sweats at midday, and proper shoes maybe ten times a year. Maybe five times. For long-distance flights I dress like I am on my way to a fourth-grade sleepover.
Still, I don’t reject the idea that style matters. It’s wrong to believe that fashion is frivolous; if someone is allowed to set money on fire buying Browns season tickets, I can accept someone setting money on fire spending $50 on a T-shirt. I too like to feel stylish, and sometimes I can allow myself the illusion that I actually know what I am doing. I believe there’s some benefit: a confidence both internal and projected. The designer Tom Ford has said that a suit is a form of armor, that when a man is well dressed, it provides an aura of invincibility that helps get him through the day. I am with Tom Ford on that, though I know I am not well-dressed enough to be Tom Ford’s cable guy.
I care enough to look like I care enough. I know I will never be confused with Clooney in Venice, but I do not want to look like a man who ran out onto the street because the meth lab was on fire. I spent more than five years working at GQ; some of it had to stick. I own a not insignificant number of blazers. I like tweed. I will wear a tie for no good reason. If this is starting to sound like bragging, I also spent the majority of the Super Bowl in 2014 walking around the press box with chocolate frosting all over my tie. Nobody said a thing. Yes, I cleaned the tie by licking off the frosting—don’t be insane.
As I’ve gotten older I’ve realized that I am somewhere between being stylistically together and stylistically a mess. I’m a type, actually. Nobody likes to think they’re a type, that they belong to any declared fashion subset—it diminishes individuality and makes it seem like individual choice is not a choice. But I’m okay with admitting that I belong to a familiar subset: the Slightly Exhausted Hipster Idiot Dad. We are everywhere, a cliché unto ourselves, easy to ridicule and recognize. You can find us staring at smartphones on playgrounds and soccer sidelines, or spending too long looking at the beer in the supermarket. All our clothes are a shade too tight for our flabby dad bodies, because we are vain, believe that we will return to being ripped like we were at twenty-three, believe we are not ready to wear relaxed-fit jeans. Even if we are completely ready for relaxed-fit jeans. Even if relaxed-fit jeans would make us somewhere between 40 and 50 percent happier. The Slightly Exhausted Hipster Idiot Dad has a haircut that cost more than eight bucks, a haircut that the Hipster Idiot Dad actually thought about before sitting in the barber’s chair. It might not even be a barber. It might be a salon. The Slightly Exhausted Hipster Idiot Dad cares a little too much about sneakers. We own more than three hooded sweatshirts. There are at least two T-shirts in the closet that we have hung on to for twenty years and love as much as our children. One is an R.E.M. T-shirt. Neither fits (flab). When the Slightly Exhausted Hipster Idiot Dad has to prepare for a Big Night Out, it usually involves jeans and the Good Collared Shirt. The Good Collared Shirt lives in a slightly less occupied part of the closet. It is reasonably flattering and has been complimented at least once by a stranger. The Slightly Exhausted Hipster Idiot Dad’s wife likes it. Or at least tolerates it. There is also a stain on the front pocket that may or may not be hummus, but the Slightly Exhausted Hipster Idiot Dad is at least 70 percent sure nobody can see it. This is not true. Everyone can see it.
The Slightly Exhausted Hipster Idiot Dad is representative of fatigue, not surrender. He is at least one stage before Giving Up. Giving Up is sweats with no underpants to the airport. Giving Up is going to your mother’s house on Christmas Day in a Dolphins jersey.
I am not there. Yet. But a Dolphins jersey sounds pretty comfortable.
★ During a twelve-month stretch between 2012 and 2013, I didn’t buy any new clothes. For a year. As a test. One day I looked in my closet and saw the billowing piles of T-shirts and sweaters and realized, This is cuckoo. I don’t need this. I gave a lot of clothes away. I did not buy anything in stores or online. Okay, that is not totally true: I bought a pair of tennis shorts. I bought a winter hat at the Super Bowl. But that was pretty much it. It was a liberation. It is amazing how much time frees up when you do not have to shop for clothes. You could learn to play a musical instrument in the time you spend shopping for and buying clothes. I did not learn to play a musical instrument. I farted around. When I wanted to wear something “new,” I would dig into that overstuffed closet and find something I’d completely forgotten I owned. I am telling you right now: 20 percent of what’s in your closet is things you have forgotten you own. It’s like getting a new wardrobe you don’t have to pay for.
When the year was up, I went back to old habits. I’m back to being a disaster. I buy things I don’t need online. I buy sweatshirts for my sweatshirts, like I am concerned that my sweatshirts need friends.
★ I have even grown to love the Waiting Chair. Everyone has sat in the Waiting Chair watching somebody else—usually a spouse—shop. There should be a coffee-table book dedicated to Waiting Chairs all over the planet. But I wonder if my appreciation of the Waiting Chair is completely tied to the invention of the smartphone. I don’t even remember the Waiting Chair before the smartphone. What did people do in the Waiting Chair before they could go onto e-mail and Facebook and text and play Temple Run? Did they just sit there in the Waiting Chair? Think? Be alone with their thoughts? Count the rivets in the ceiling of Anthropologie?
★ When you have a kid, it is your first opportunity to dress someone else, unless you are a stylist or one of those controlling lunatics who lays out your partner’s clothes on the bed. Kids’ clothes are astonishingly current and cool today. By four months, your child will be dressing better than you do. This does not change for the rest of your life.
★ A word about cargo pants. Society says you are supposed to stop wearing cargo pants as soon as you graduate from college and maaaaaybe one summer bopping around Copenhagen with a long-tailed white rat living in one of the side pockets. I still wear cargo pants, however. I like them and I don’t care if people think the pockets are full of bong water. My wife chooses to ignore them, as if we’re living in a Cheever story and the cargo pants are a secret family I have in Westport, Connecticut.
★ I am okay with logos, but I don’t like those sports T-shirts that say stuff like Let’s Sweat and It’s Biceps Time and Second Place Is for Llamas. Nike has made a national affliction of these. I am okay if you want to tell everyone you went to Middlebury or the Grand Canyon or you like the oysters at the Little Oyster Hut, but I don’t want a shirt to make an announcement about my athleticism or my tenacity or my intention to sweat all over you. Plus the directives seem to be going in the wrong direction. Aren’t you supposed to be motivating yourself?
★ I may have come up with Second Place Is for Llamas on my own, and truthfully, I would wear that.
★ Conversely, I’m a fan of Accomplishment Wear from athletic achievements, whether it’s a T-shirt signaling participation in a 5K or a New Year’s Day plunge or one of those obstacle courses in which you crawl under barbed wire and ex-commandos shout mean things about your mother and your 401K. I refuse to pooh-pooh Accomplishment Wear. I support anything that encourages people to be active. You crawled over the finish of the Towson Turkey Trot after drinking five old-fashioneds the night before? Good for you. I’m awestruck and proud of you.
★ If you have to ask, “Do I look good in this cowboy hat?” please do not wear a cowboy hat.
★ On a visit home, my brother bought a Harvard sweatshirt as sort of a joke, since neither of us was close to Harvard material. But I wore it a couple times and it was an odd experience. It’s sort of flaunty in the wrong ways. You wear a Wisconsin sweatshirt and people are kind of like, “Hey, Badger”—it’s totally harmless and unbraggy, like telling people you like picnic tables and kegs. But a Harvard sweatshirt sends a different message. It’s like walking into a room and saying, Hey, I am very smart or My parents know people. I felt like I was going to get pulled over by the campus police or hired to write for a late-night comedy show.
★ As a sportswriter, I am very familiar with the great American ritual of wearing a sports jersey to a football game, and I have made my peace with it. I know there is a sect out there that believes that athletic apparel is for kids, that once you are able to get your learner’s permit you probably should stop walking around in that Dolphins jersey. This is not necessarily wrong; it’s just too late. It’s unenforceable. We are not going back to the old days of people in gray hats watching ballgames. It is not coming back. Don Draper is not taking you to the Yankees. Don Draper’s grandson, Booger Draper, is, and he’s wearing a Jorge Posada jersey.
★ Booger Draper is a great name for a band.
★ In my early twenties I went through a T-shirt-and-vest period. I don’t mean a sweater vest. I mean a black cotton vest, with a T-shirt under it, sometimes worn with shorts and boots. I looked like Blossom hiking on the Appalachian Trail.
★ What is enraging about these periods in your life is, nobody says anything to you. They don’t say anything because it’s not polite, of course, but maybe we should say things. I would have really liked it if someone had pulled me aside and told me to stop wearing the black cotton vest and saved me from about three dozen really embarrassing photographs I cannot hang on the wall.
★ I also had a green cotton vest. I had two cotton vests. Seriously, why didn’t somebody say something?
★ I once interviewed Tom Ford for a magazine story, and I put a lot of anxiety into what I’d wear that day—I’d brought my good suit, my good shirt, my good tie, which looked great to me but probably looked to him like I’d gotten dressed outside his office in the back of a van. Packing at the last minute, I’d rushed and thrown in a pair of novelty socks I’d gotten at Christmas. They were socks that had the days of the week written on them. And in the middle of this very serious interview, with arguably one of the most important voices in global fashion, a man so impeccable he looks like an Academy Award statue, Tom Ford looks at me and says, “What day is your sock?” I had no idea what he was talking about until I thought, Oh dear. Worse: the sock said THURSDAY. It was Wednesday.
★ You’re in Tokyo,” Tom Ford said. “It’s Thursday in Tokyo.”
★ I have not worn the day-of-the-week socks since.
★ To this point: avoid any “special” item. If you have a special tie or special socks or a special hat, there is somewhere between a 100 percent chance and a 100 percent chance that it is horrible. Nobody’s special socks are black. Nobody’s special tie is a simple knit navy-blue tie. The favorite socks have days of the week on them or chili lights wrapped around a statue of Mr. Spock. A favorite tie has a map of Las Vegas and a burlesque dancer on the back. Favorites are gifts to be worn the moment they are opened and then hidden in a drawer forever or hidden in the backyard under a foot of stone.
★ Your spouse already knows this, by the way. Your spouse has wanted to throw out your favorite hat since 1998.
★ I do not know if I am office-uniform material. In my life I have known several people who have embraced the office uniform: the idea of wearing basically the same exact thing to work every day. I read that the movie director Christopher Nolan goes with an office uniform. Mark Zuckerberg basically does. My old editor Peter went with navy blazer, plain-front khakis, Oxford shirt. It does simplify things. It seems less stressful. I once stayed at a house where I opened the closet and discovered that the owner had left a top row of jeans and a bottom row of black T-shirts. That was it! That is an unagonizing closet. After everyone realizes you’re in the same outfit day in and day out, the novelty fades. When you do mix it up, it is a big deal. (When Peter wore an entire khaki suit, he looked like he was going to take an ocean liner to the Cannes Film Festival.) I just think I lack the discipline. I’d fail immediately. I’d do three days with the same T-shirt and jeans and a blazer and then I’d panic and wear a rabbit costume.
★ Things I can pull off:
1. Sneakers with a suit.
2. Tie bar.
3. Toddler pizza vomit on T-shirt.
★ Things I cannot pull off:
1. Jorts.
2. Collarless shirts.
3. Monocle.
★ Act like you meant to do that. Once I spent a day following around a celebrity stylist who dressed actors and actresses for the Oscars and bar mitzvahs and talk-show appearances and all that. We sat on a bench across from the Plaza Hotel on Fifth Avenue and watched the Manhattan crowd stroll by. It was early September, with enough of a crisp breeze that New Yorkers could finally surrender the flip-flops and resemble stylish humans, and it was fun and anthropological to sit with an expert and pay close attention to what people were wearing. This stylist offered a bit of advice that has always stuck, which was, whatever you do, look like you meant to do it. It is wise advice.
★ Looking like you meant to do it requires no cash or even expertise, just enough of a rush of confidence that whatever you are wearing, you intended. If your pants are six inches above the ankle, you meant to do that. If your dress has a rip down the side from accidentally bumping into the company snack machine, you meant to do that. Projection of confidence is 90 percent of the deal, the stylist assured me.
★ I know this doesn’t excuse my cargo pants, but I don’t care. I meant to do it.