The Best $45 You’ll Ever Spend on Sneakers

4 min read

Shop$65 $45, amazon.com

Welcome to the Esquire Endorsement. Heavily researched. Thoroughly vetted. These picks are the best way to spend your hard-earned cash.

Tear down that sneaker wall. Clean out the bottom of your closet. Sell those stupid limited releases. Before you get mad at that or comment on the crusty old sneakers in the lead photo (author’s own), I’ll go ahead and confirm your suspicions: I take a smug pride in this opinion. I’m Catholic, so I do consider this smugness a stain on my soul. Anytime I hit that confessional or fold my hands, I say, “Father forgive me because I’ve looked down on my fellow man. I’ve looked down on those who spend their hard-earned money on sneakers.” It’s not something I should think. If you are a sneakerhead, you’d be in the right to hate me; I accept that. But aren’t you at all interested in hearing me out?

In my mind, the sneaker was perfected with the Converse Chuck Taylor, the high-top. There have been attempts to upgrade the Chuck Taylor—the Chuck 70 and the First String—and I don’t care for any of them. The OG can’t be beat. The slimmer silhouette and high-top look as good with shorts as with pants. They’re cheap. You can beat them up. They’re great for a workout, and fine for anything that’s not a timed run or hardcore pickup game. And, crucially, you can find them in any city in America. In a culture based on limited-run releases, the Chuck Taylor is the last great everyman sneaker.

I’m All Good on the Sneaker Re-Issue Cycle

When I was a kid, I spent plenty of paychecks on Yeezys and Air Maxes. It was a core part of what got my friends and me into fashion. I don’t think there’s anything wrong with caring about and buying sneakers, but if you’re hunting for Hokas or chasing the hottest fashion sneakers, I assume you’re the victim of the marketing machine. I’ve been conscious of this stuff for a decade at this point, and I’ve already lived through numerous re-issues of Tinker Hatfield designs. You are being sold the same thing over and over while being told it’s exclusive and you have to have it. Why not just buy a style that doesn’t have to be re-promoted?

That’s what I decided a few years ago when thinking about spending well-over $200 for rubber soles, synthetic uppers, and designs that are recycled at an increasingly high clip—I decided I rather just go back to the source. The only sneakers I find compelling these days are a handful of the Adidas models for NBA players, like the Anthony Edwards shoes. Besides that, it’s all the same stuff. Instead of reading about the newest re-release and having to digitally stand in line with resellers at 10 a.m. on a Saturday morning, I just decided to move on. I assume Converse will make the same black and white Chuck Taylors until the day I die.

Shop$65 $45, amazon.com

They Are Comfortable (I Swear)

The only critique of the classic Chuck Taylors that I will entertain is the slimness of the shoe. If you have wide feet, they run narrow. There’s a wide version now, but I know some people still have difficulty with that. I understand that, and I give y’all full freedom to wear your Hokas or your Ons.

But if you’re able bodied, not seriously wide-footed, and not doing any serious running in your shoes, do you really need all that cushion? Don’t you think you’ve been oversold on the comfort front? Sure, get the running shoes for your marathon training and the basketball sneakers for your weekly pickups, but don’t act like you’re on your feet so damn much that you can’t wear some thin-soled Chucks. I wear mine for weightlifting and my weekly runs—high-impact sprints, you’d be surprised at how quickly your ankles strengthen when you’re not over-cushioned. Your dad wore them, his dad wore them, and they came out alright.

Shop$65 $45, amazon.com

Good-Looking, Versatile, and You Can Get ‘Em Anywhere

But the heart of my argument comes back to availability and the myriad of ways you can wear them. After being obsessed with limited releases I could never afford and re-issued colorways I could never get my hands on, I kind of just checked out of sneaker culture. Right this second, I could walk into my childhood mall and go to Journey’s. They will, without a doubt, have some Chucks, and they will have them in my size. I can buy them and wear them out of the store, and I can do that anywhere in America. For me, that’s what a sneaker should be.

And because they’re so easy to get, I don’t have to store them in a climate-controlled system. I don’t have to worry about dry rot. I don’t have to worry about scuffs or creases. I don’t have to worry about water and sand when I wear them to the beach. When a pair is beat up, they become yard-work Chucks. When there’s a hole in the canvas, they go in the trash. I stopped making sneakers the focus of my wardrobe, the focus of my life. That, reader, has made all the difference.

Shop$65 $45, amazon.com

Photographs by Florence Sullivan