The road to pulling off cool sneakers is paved with questionable styling decisions and purchases. First, I looked for inspirations. The best pictures I’d seen of someone in the Vapormaxes were from the shoe’s ad campaign, starring Acronym designer Errolson Hugh and John Mayer. They were dressed in cowboy hats and artisan robes, probably from Visvim. They looked like John Wayne cast in an alien flick, a look I had no hope of pulling off (or affording). I talked to a coworker in a similar situation: he’d also bought a pair of shoes he loved, but couldn’t figure out. He said he just...never wore them. So that was one option. The other was significantly more ambitious, and verging on dumb: re-engineering everything else about myself to fit in with my new sneakers. That’s the one I chose.

I emerged from the department store bathroom-cum-changing room, in black Uniqlo drawstring trousers and a black Uniqlo U (the Christophe Lemaire-designed line) T-shirt. I set the difficulty all the way down to rookie with the all-black outfit but after approaching my girlfriend with the amount of sheepishness required by a mid-day outfit change, even she agreed I was at least pulling off the shoes now. I didn’t immediately change into it, but I also bought a white Uniqlo U shirt during my desperate trip. Purchases since are less frenzied but equally pressurized. At a COS last week, it was easy to talk myself into spending a couple hundred dollars on a sleek new hybrid tote and backpack so that I could get rid of my old dusty bag plus a new jacket with several pockets. When I showed my editor the new outerwear, he immediately noted that it would go well with my Vapormaxes. Mission accomplished.

In a roundabout way, I’m grasping at that intangible energy with these shoes, hoping the confidence can seep over into other parts of my life and wardrobe.

I imagine a lot of guys around the world have been faced with this same conundrum over the past year or so. As sneakers start to look more like absurd fun-house mirror versions of the shoes most guys have been wearing their whole lives, they’ve gotten much more difficult to wear. If the slip-ons, Nike runners, and Common Projects most guys grew up on are the Toyota Camrys of the sneaker world—simple, elegant, functional—a buzzed-about shoe like Balenciaga’s Triple S is a monster truck. Even before they made others question your political leanings, Yeezys sucked the oxygen out of entire outfits. These are shoes that demand all the attention—and, probably, an overhauled wardrobe to wear them. Plenty of guys have already gone through the very same process of changing their clothes to match their sneakers. Wearing jeans with your cool sneakers isn’t exactly easy—as evidenced by the three million-plus people who have watched this video tutorial on pinrolling jeans. I blame the emergence of the jogger, a sweatpant that cinches right above the ankles, on our obsession with shoes. Joggers are the cheat code of pants: they make your shoes look great by sacrificing any sort of style in the process.

And in 2018, it’s easy to buy shoes without actually taking the time to consider putting them on your feet. When I first bought my pair, I wasn’t actually confronted with the reality of wearing them: the listing doesn’t really show them on feet—so they remain a beautiful art piece framed by hype. Going into a sneaker purchase blind isn’t unusual. By the time a shoe releases, the actual look and style of the sneaker has been pushed down the list of considerations. A shoe designed by someone like Virgil Abloh or Kanye West comes cocooned in so much hype that it’s basically critic-proof, and the really fire shoes are collectively anointed as the next cool thing weeks before an official drop. Before anyone can buy them, they’ve already been deemed incredibly valuable. So actually purchasing requires mammoth effort: joining raffles, tagging friends on Instagram, declaring yourself “in the zone,” downloading specialty apps, or draining a savings account to buy on the secondary market. It’s easy to forget that in the end these are items to be worn. I certainly did.

But wearing these shoes pokes at a deep down part of me, one that I want to bring to the surface. The best-dressed people in the world don’t just have great taste, they’re also incredibly confident. In a roundabout way, I’m grasping at that intangible energy with these shoes, hoping the confidence can seep over into other parts of my life and wardrobe. These shoes scare me a little bit, and that feels like exactly the point. They don’t just force me to wear something out of my comfort zone on my feet, but to reconsider and recalibrate my closet with all sorts of things that scare me. I don’t need jeans; I need these Nike ACG cargo pants with a built-in looping nylon belt. I don’t want to wear khakis anymore; I need to get these ridiculous Kapital pants that are 75 percent pockets.

Before I completely rebuild my wardrobe, though, I’m making do with what I already own. The other weekend I stared at the clothes currently in my possession, in the same spot where the anxiety typically hits. But instead of balking I ended up saying screw it, and pulling out a pair of washed-out jeans to wear with my Vapormaxes. I looked in the mirror. Did it look great? Not really. Did it meet the qualifications for what I thought should be worn with the sneakers? Not at all. But I walked out the door anyway. Best of all: as I walked down the street, no one I passed on the sidewalk seemed to care.