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How I Finally Bought a Wardrobe That Doesn’t Make Teenagers Laugh

You don’t have to give up comfort to dress like a grownup

Clothing consisting of black t-shirt, brown leather belt, brown chelsea boots, dark blue jeans, and gray wool pea coat.
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Let me tell you about my drug dealer outfit. 

Last summer at the beach, I thought I’d found the perfect sartorial solution to my mortal fear of melanoma when my 17-year-old gestured lovingly toward my floppy bucket hat and sunglasses and sniffed, “Whoa, where’s the tracksuit, Pablo Escobar?”

Supportive comments of this type—I call them Gen Zingers—have become more frequent of late in the public corridors of my home. 

Take, “Are you unironically wearing New Balance sneakers right now?” Or, “Wait, I did not know that drawstring pants were a real thing.” Or perhaps my favorite (upon seeing me in a powder blue Ralph Lauren button-down tucked into black Levi’s 501s): “Just no.” 

Blame it on the pandemic or a couple of decades of marriage or the long-ago suspension of all my men’s mag subscriptions—I’ve gotten so comfortable dressing comfortably that I’ve become an actual fashion don’t

If I’m “dressing for the job I want,” I must want to be a mall walker. Even khaki pleats still think they can get fresh with me. 

And so, as humans began leaving their Netflix shelters and intermingling again this year, I decided to take a harder look at the squishiness of my style choices. 

Patrick Kenger is a men’s image consultant whose fashion and grooming articles make me feel even schlubbier than I appear to my disrespecting teenager. But I figured that Kenger could advise me on what to avoid and how to upgrade so I could at least get out the door without snaring a razored barb.

I won’t burden you with every detail about why you should never again wear zip-off pants or anything with a logo (“Repeat after me,” Kenger says. “After 50, you are not someone’s billboard.”). But his overall message really made an impact, and it’s helped immeasurably to squelch the wisecracks. 

Try dressing “a little bit better,” he advises, simply by paying attention. 

If your pants are bagging, get them hemmed. In fact, tailor nearly everything, since “good-fitting clothing solves 80 percent of looking great,” he says. 

If your T-shirt has yellow underarms, your pants are stained or your socks are orphans, trash them. If the last winter coat you bought is old enough to drive, buy a new one. Avoid anything too flashy or faddish—or anything with “Ed” and “Hardy” on the garment—and if you spend serious money on any item, for God's sake, make it your shoes. 

I’m still not George Clooney but it’s been a month since the resident fashion police hassled me about an athleisure-wear infraction. I’ve gone back to basics: clean white and black T-shirts that fit well; pants with the slightest bit of stretch in them (no, I did not say skinny jeans), and a new pair of Chelsea boots that are the most versatile and on-the-money wardrobe addition I’ve bought in years. 

Know how I know? My son, who’s also a size 10, said the other day—unironically—“Dad, can I borrow those shoes?”