When I was a kid and lived on West 72nd Street in Manhattan, I wanted a pair of the original Air Jordans—the red and black ones that the NBA had banned for being too flashy or some shit. There was a mom-and-pop sneaker shop on the Upper West Side that showed them off in their windows, and I’d salivate at the sight of them, but my sensible, frugal, single mother was of the opinion that 50 bucks was way too much money for a pair of sneakers and wouldn’t cave. (She would, however, try to make me feel better by trying to be hip from there on out. “Ooh, look, Sammy! He’s wearing Jordans!” she’d say. I would quickly correct her: “No, Mom, those are Jordache.”) It’s all pretty wild to think about now that I’m a grown-ass man and I can buy my own sneakers, which generally cost a hell of a lot more than 50 dollars.

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The great thing about sneakers in 2015 is that it’s actually acceptable to wear them with anything and almost anywhere. Believe it or not, it’s also possible to wear sneakers that look as “hip” as my mom found them to be back then without defaulting to the Sad Gym Coach look you might be working with now. First things first, though.

You Should Have Two Pairs

There are two types of sneakers that everyone should have:

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“Beaters.” These are the ones you’re willing to let get dirty. Wear them when you’re mowing your lawn or changing your oil. Your new beaters are what you’re wearing on your feet right now as you read this. Matter of fact, take those pieces of Target shit off your feet and throw them out. Like, now. No, really, those aren’t even good enough to be Beaters.

The Everyday Pair: Here are the shoes that you can wear in the real world, whether you’re working out or hanging out with friends. They look good out of the box, of course, but also even after a few months of wear. (Personally, I love the look of a well-worn sneaker. It gives it some character. It’s the Randall “Tex” Cobb of footwear.) So, what should you look for in an everyday shoe?

Consider Your Age

Being a mature, fully grown adult, I find it difficult to casually wear sneakers branded by basketball players who are younger than me. The same thing goes for sports jerseys. Actually, skip wearing jerseys—outside of actual sporting events, where it’s only kind of okay—altogether. Please remember that Kyrie, Russell, LeBron, and so forth are all great players, but they’re young. Like, super young. Kyrie just turned 14 this year.

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If you want to be the old man wearing the signature shoe of a player who is 20 years younger than you, know that even buying a Corvette is a less cheesy way to approach your mid-life crisis. The only time it’s actually acceptable to wear a baby athlete’s signature shoes is if you use them for actually playing sports, because the fancy newer models sometimes do have a better fit, with ideal comfort and arch support. But player shoes still tend to be showier than they need to be. Given that Kobe Bryant is close to 50, you can wear his shoes, but they’re still fucking wack, and will make you look like a weirdo 40-year-old raver who cashed out his 401k to buy a shitload of molly and move to Ibiza.

Think Classic And Versatile

Shoes like Air Force Ones, Vans Eras, or even (gulp) Stan Smiths are great everyday shoes. My one problem with Stan Smiths is that here in New York City, EVERYONE wears them. They are to sneakers what those big floppy hats are to headwear. Here, everyone takes mass transit: Eye contact is frowned upon and on certain trains will get you murked. Because of this, we spend a lot of time looking at people’s feet. You want a sneaker that’s classic, yet a wee bit eye-catching. Maybe some hints of red or a splash of blue. And fuck that whole “No White After Labor Day” belief. Basically, you want something that won’t make a high school kid stop you in the street and shout, “WHAT ARE THOOOOOOSE?!”

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Buy what you like, but get something practical and stylish. My personal preference are Nikes, and have been since I was a brainwashed youth. I like the way they fit and feel. I don’t do the Vans thing much, as they offer no support on arches, and they’re as flimsy as the hard crust on Jello. Generally, stay away from sneakers sold by stores that don’t specialize in them, like Urban Outfitters. They might have cool stuff, but don’t be one of those kids who pair ’em with ironic high shorts and silly socks. No Saucony, either.

The Upside To Retros

Retros are great if you were a ’90s kid: Yes, they might be silly, but now you can buy the shoes from your childhood that maybe your family couldn’t afford, or maybe weren’t available in your small town, and maybe that’s enough of a reason to pick up a pair. I’ve pretty much retired from sneaker collecting, but I did buy the AIR TECH CHALLENGE 2, only because I loved them as a kid but never owned them. They look great with anything, except that whole new sweatpants trend I could give a flying fuck about. I’ve worn the same pair for almost half a year, and my younger and much cooler roommate still asks if I got new shoes every time I wear them. Plus, they prove that retros can sometimes inform current fashion trends, too: Kanye’s Air Yeezy 2’s use the same bottoms.

Jordans in their original colorways—meaning, sneakers that Michael Jordan himself actually wore or played in— are great, though nowadays reissues sell out relatively fast, and reseller markup is kinda pricey. (As for the newer, weirder colorways, they don’t look nearly as good.) But they’re a great example of simple, classic shoes: Think anything without a strap, velcro, or some other weird BDSM contraption. Asics Gel Lytes, New Balances, and Pumas all work.

The Downside To Retros

The quality. The new leather on retro shoes is usually absolutely dreadful. Have you noticed how many NBA players playing in retros have had total shoe meltdowns? Most likely this is because Nike cranks out them out to the tune of two to three pairs a month in colors raging from the original style to some sort of neon gangbang. For a safer alternative, Nike released the Air Jordan 2015 Remastered line earlier this year, providing a small sprinkling of various popular Jordans with newer, higher-quality materials.

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The hype. When a retro sneaker—especially a new Jordan model—drops, it’s generally pure and utter chaos. The sneaker blogs have spent the past year hyping the shoe so hard that people are rabid for them on the first day of release. Add the fact that your favorite rapper cosigned them, and you’re pretty much fucked. Either you’re gonna camp out for a pair (nope), pay out the ass for them on eBay or at consignment shops (nope), or cross your fingers that Nike or whoever does a random restock one day (doubt it).

The colors. When it comes to most retros, I’m a purist. Meaning if I wear a pair of Bo Jacksons or the greatest shoe ever made, they better look like the original pair I got back in the day. It bears repeating: There’s a reason Michael Jordan never played in glow-in-the-dark/patent leather/polka-dotted sneakers. He’s not a fucking dickbag. (Oh, wait.)

So, Where Do You Buy Sneakers?

The internet is a magical place for sneakers of all colors and sizes. I prefer online shopping for a few reasons. First, I can do it at work, when I should be working. Second, shopping malls (where sneaker stores generally still reside) fucking suck, unless the mall also has an Orange Julius. And finally, the internet has it all, not just one store’s current stock. I generally tend to stay away from Ebay, though. While you can find pretty much any sneaker imaginable, the prices are generally marked the fuck up, as is shipping, plus fakes are always an issue. Unless, of course, you don’t have a problem wearing something from Miakel Jardins’ signature line.

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So here’s where to go instead.

1. Sneakerhead Sites

  • Nice Kicks. This is my crack. It’s the best site on the web. It tells you what’s coming out, offers release dates, and caps it off with well-put-together videos. Yes, I bitched before about the hyping of shoes, but this isn’t a hype-based site: It’s for people who are generally into sneakers and the culture. Also, the EIC, George Kiel III, seems like a genuinely nice dude, not some jerkoff who’s wearing what’s new just ’cause it’s new.
  • Kicks Deals. Basically, this is where all the super-hyped shoes go to die. Which means price deals aplenty, from “free shipping” to “half off.”
  • Sole Collector. Just like Nick Kicks, this is a great site about the culture, with a great buy/sell/trade section. I’ve bought a few pairs from other sneakerheads through meetups; I will say, though, that having a 14-year-old Puerto Rican kid from Queens show up at Gawker Media HQ with shoeboxes is kinda suspect, so choose your meet ups wiser.
  • Hypebeast. This place has been around for a long-ass time, and odds are that guy on the train with the Hood By Air leather straitjacket/drop-crotch pant-skirt hybrid wakes up and checks it first thing in the morning. There aren’t as much sneaker posts as there used to be, but the ones you get generally involve high-quality, exclusive pics, and the comments are still the best. It’s like online Call of Duty come to life.
  • Flight Club. This place—which is both a website and a series of real places—theoretically has every hard-to-find and limited-edition sneaker ever made, though, I couldn’t get a pair of white Uptowns for last year’s Christmas party. They do, however, have multiple pairs of the Marty Mcfly Nike Air Mags. Let me repeat: They have multiple pairs of AIR MAGS. One time when I was in the NYC location, Iman Shumpert bought a pair, but how much good luck that brought him. Expect to pay a little more for stuff here due to the fact that it’s a consignment shop; if you’re in New York or L.A., it’s worth dropping in just to see the 14-year-old Upper West Side kids decked out in their best Supreme gear trying to show off ... in a fucking retail store.

2. Instagram or Twitter. I know, I know, it sounds incredibly dumb. Considering we’re all socially awkward and might not stop someone to say, “Hey, where’d you get those!” in person, try the next best thing. Do a hashtag search and roll the dice, but be prepared to get lost in a vortex of misspelled words and horrible descriptions, from #nikerealshit to #youaintaboutthislyfe.

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3. Actual chain brands. Yeah, Foot Locker, Finish Line, Champs and the like. Man, fuck big business, though. As someone who grew up only going to mom-and-pop joints to buy my shoes, this is the absolute last option for me.

Never Ever, Ever Buy The Following

1. Nike Foamposites: These are the absolute worst shoes. Only your drug dealer wears them, and he’s your backup-to-the-backup drug dealer. They’re straight carbonite and cost around $200.

2. Any combination of neon and patent leather: If I have to explain this to you, grab those Target-ass shoes out of the trash and put them back on your feet. You’re an adult.

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3. High-end fashion-designer schemes. Which is to say, any sneakers not made by sneaker companies. Kevin Hart is Patient Zero of this disease. Look at any picture of the guy doing press shit to see what I mean. It’s great that you wanna floss and show the world you’re still hip, but your so-called “adult sneakers” cost a billion dollars, plus Justin Bieber wears them. Also, keep in mind that John Galliano doesn’t have a championship ring.

Parting Thoughts

These are going to be your shoes for the next, oh, I don’t know, four to five months, so think practical. Yes, you want to have to some flair and look good, but remember: These things are going to be on your feet. I suggest maybe a Dr. Scholl’s insert or some comfortable socks as well. If you’re in a walking city like NYC, your shits WILL get scuffed, but as I said, wear and tear gives shoes character. Keep them in decent condition, though, which is to say, keep ’em in the box. And for the love of God, don’t choke your feet by lacing them up too tight.


Sam Woolley is an illustrator for Gawker Media.