Sneakerheads 101: How To Start Collecting Sneakers & Get Into The Kicks Game

In one form or another, sneakers have been around for more than a century, believe it or not. From the original “plimsolls” of the 1870s, featuring a rubber outsole and a canvas upper, to Kanye West’s signature adidas Yeezy line featuring shoes that may look more at-home in a sci-fi movie, the trusty trainer has come along way.

Let’s say you’re interested in broadening your footwear horizons a little, maybe expanding your selections to include some more sneakers. But with a historical catalog stretching back literally decades, how does the aspiring sneakerhead know where to start?

We’ve got your back. The Fresh Press has assembled a crack panel of sneaker historians, industry experts and long-time lovers of kicks and asked them to take a look back at the first pair that set their hearts afire, how to start collecting sneakers, and how to find the right pair(s) for you.

Russ Bengtson — Former editor-in-chief of SLAM Magazine and Complex sneaker editor, author of the forthcoming ‘History of Basketball in 15 Sneakers.’
Madison Hartman — Social director for New York-based consignment store Stadium Goods.
Michael Sykes II — Writer at USA Today’s For The Win, editor-in-chief of The Kicks You Wear twice-weekly newsletter.
Nitzan Bluvstein — Count The Dings podcaster & contributor for The Athletic’s Daily Ding.
Will Hardison — Writer for sneaker and streetwear retailer DTLR VILLA.
Mike Taddow — Sneaker collector since 1991.

Russ Bengtson: This is actually a tougher question than it seems because my memory sucks now. The first pair I remember really wanting and getting was a pair of Nike Bruins when I was in fourth grade or thereabouts—this would have been before “Nike Air” was even a thing I knew about, either the late ’70s or early ’80s. I wore those until they literally fell apart. A few years later I asked for the original Air Jordans and haha, no. I was into adult sizes by then and they were $65. Wound up with a $35 pair of Air Ships from Marshalls instead. Like Mike, only earlier.
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Madison Hartman: Growing up in the suburbs during the early aughts, Etnies and DC shoes were all the rage at my middle school. I desperately wanted a pair, but I was raised by a bargain shopper. Luckily the local outlet mall had a few bargain sneaker stores, so I managed to convince my mom to buy me a pair of white Etnies with a pink “E” logo. Sadly, my dedication to skateboarding lasted all of 6 months, at which point I broke my arm while skating in my garage.
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Michael Sykes II: I remember this like it was yesterday. I was in third grade at the time and a huge Allen Iverson fan. The Answer IVs had just dropped and I wanted them badly. I remember seeing them in the Eastbay catalog we’d get at the crib and begging my folks for them every day for, like, three months. My birthday came and I finally got them. That’s probably where this all started for me.
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Nitzan Bluvstein: Heelys. (Ed. note: Uhhh…ma’am?) Okay, stay with me on this one because I know those shoes don’t give off even an ounce of “cool” but a) I wasn’t cool, I just knew what I wanted and b) the concept that your shoes could just magically turn into faux roller blades was the most late 90’s/early 00’s thing you could ask for. And no. No chance I got them because in reality they were basically just another toy. But those commercials were iconic.
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Will Hardison: I was in the 7th grade and begged my parents for the original Air Jordan 12s in Obsidian/White-French Blue. Man, those were a beautiful shoe. Unfortunately, my begging didn’t work and I was unable to convince my parents to shell out the money. However, I didn’t give up and they finally caved when the black/red pair released a few months later and I still have the pair to this day.
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Mike Taddow: 13-year-old me wanted a pair of Air Command Forces in 1991. My parents thought otherwise, so no, no I didn’t get them.

RB: I’d say get something versatile and don’t put all your money towards one crazy pair, unless there’s one you absolutely want more than anything. You’re better off with a few pairs that fill different needs (a pair of runners, a pair of retro hoops shoes, a pair of current signature shoes) than one pair of super-expensive, super-exclusive joints that you’re going to stress over every time you wear them out the door.
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MH: First and foremost, don’t buy sneakers that aren’t comfortable. The flashy, no-cushion sneakers I’ve bought sit in boxes while the cozy stuff stays in my weekly rotation, hype or no hype. Second, fads come and go just buy what you like and don’t worry about chasing down every trend.
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MS: Be wary of price and try not to spend too much on kicks you might not even like in a month or two. It’s so easy to spend $100 or more to buy a shoe on resale right now. But if you don’t know a ton about that shoe or how it fits and how it looks on foot, you have to be wary.
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NB: The best advice I ever got when I was first getting into sneakers was “get whatever the hell you want.” For example, once I was obsessed with the Air Max 97 in Mustard — I texted every great sneakerhead I know and some friends for their honest opinion. And the funniest thing is friends gave their opinions (as asked, fine) but the folks I’d met within the sneaker industry all came back with the same “if you like it, get it.”
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WH: Don’t settle. In my opinion, your first couple pairs of sneakers should be versatile. Take my black/red 12s for example. It’s a shoe that doesn’t go with much other than black and red and to be honest, I didn’t wear them as much as I probably should have for them being my first pair. Your shoes are meant to be worn, so select a few pairs that you’ll wear and wear often.
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MT: Never buy sneakers because everyone is talking about them. Buy them if (a) YOU think they’re cool, (b) they feel good on feet, and (c) you can afford them.

RB: Air Jordan 1 highs. The OG colors and collabs are all prohibitively expensive, but they make enough different ones now that you can always find a pair of highs on sale. And personally I’d get a pair of highs in a nontraditional colorway before I got a pair of mids in Chicago (or, for that matter, any other) colors.
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MH: Literally any Air Max. There are so many different silhouettes, colorways and collaborations that no matter what your price point or personal style is, you can find something that suits you. I also happen to think Air Max never goes out of style.
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MS: Air Max 1 or Air Max 90. It’s really hard to go wrong with most colorways there and they’re really versatile in terms of the type of ‘fit you can get off with them.
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NB: I think you can’t go wrong with Air Max, obviously. They’re a staple for a good reason, and I’ve had phases of liking the 90s over the 97s or being way too into the 95s for some time — so it’s really easy to figure out what silhouette works best for you. If you’re not super down to be polarizing with your kicks, I think the best bet is the 90s — I’m biased but the Volt and Purple colorways are incredibly cool and it’s definitely more of a chunky shoe but doesn’t feel as heavy as the 95s. They’re also not too expensive (~$120) and even though there’s definitely amazing kicks that are way cheaper, it won’t completely make your bank account cry.
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WH: Whew, tough call here. My younger self would have said the Air Jordan line but as I’ve gotten older, Vans has stolen my heart. You can’t go wrong with several pairs of Old Skool Vans in various colors.
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MT: For me, my first foray into sneaker collecting started off with trainers that could be worn casually. That was the wave in my time, so Air Max was heavy in my rotation when kicking off my collection.

RB: Don’t buy sneakers on sale just because they’re too cheap to pass up. If you weren’t willing to spend full retail on them, you’re likely never going to wear them. And wear whatever you want whenever you want because almost everything is just gonna get retroed again anyway.
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MH: Don’t worry about trying to get every single hot sneaker. Yes, sometimes it hurts on a Saturday morning when you take an L but most of the time you forget about it a few hours later. Time heals all wounds.
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MS: STOP SPENDING SO MUCH MONEY ON SHOES YOU AREN’T WEARING YOU LOOK LIKE A DOPE. Oh, and always, always, always wear your shoes. Not wearing them is wack.
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NB: Despite getting some very obvious clear advice to get what I want and forget what others think about it, it took me a second to really embrace it. Trying to get into sneakers I listened to what the voices I most enjoyed in the space were saying, instead of thinking what actually fits for me, my outfits, which kicks I think I can rock best, etc — and there were definitely some sneaker purchases I wouldn’t have made if I considered myself first before what was “cool.” For example, I look absolutely terrible in a high Air Jordan 1. The shoe itself is one of my personal favorites to see on other people, but it just doesn’t work with the outfits I’m usually putting together for myself. So, I don’t need to have it just because others do.
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WH: Don’t sell your sneakers. Yes, sometimes due to uncontrollable circumstances, we need to unload a few pairs, but hang on to as many pairs as you can. I’ve sold off most of my collection from when I was growing up and it makes me sick when I think about it. My collection was full of sneakers that all had their own story and represented my childhood. I wish I could open up my closet to find boxes full of those memories. Keep your kicks.
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MT: Diversify the colorways of kicks to make sure you have the fits to compliment them. Also, clean them carefully and let them breathe.

RB: The big thing is don’t get caught up in the whole “sneakers are an investment” thing. Figure out what you like and spend your money on that. Assume that everything you buy will be worthless someday. Wear your grails until they fall apart. And don’t turn it into a perpetual chase. If you miss out on a release, it’s fine. There’s just gonna be another one. And another one, and another one, and another one.
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MH: If the story behind a sneaker is something you connect with – whether it’s who designed it, what it was inspired by or what the collection represents – that’s far more important than what sneaker Twitter thinks of that shoe.
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MS: I would say they should try not to follow hype too much. I know it’s super duper hard, but it’s easy to get frustrated early when you’re not getting pair after pair. You might lose the love early and that stinks. So just buying cool models no one is touching is the way to go early on, in my opinion.
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NB: Well, I am just an aspiring sneakerhead. And even saying THAT is a stretch. I am just really into expressing my style with sneakers when I’m out, but I’m still discovering the rich history that sneaker culture has and how I want to interact with it. There are so many amazing voices in the space right now putting out incredible written content, photography, etc that are engaging for consumers and people trying to get excited about the world of kicks. I would say just diving into any of their brilliant work is the best way for someone to get started. I wouldn’t even be able to list all of my favorites so I’ll kick off with a short list (the sincerest apologies to anyone I forgot, there are SO many): @fearofroya on Twitter, @shoehefner5 on IG, @alex_the_don on IG, @shegotgame on IG, and @coseezy on IG are some of my personal favorites and just tuning into all of their content is the best advice I can give.
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WH: Buy what you like and ignore the hype! If you like a pair of shoes, that’s all that matters. Who cares if they’re limited, designed by so and so, or cost you $1,000. At the end of the day they are on your feet and that’s all that matters. Some of my favorite shoes are sneakers that barely anyone has ever heard of or cared about, but I like and enjoy them.
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MT: Be smart with your money. Just because you like a shoe right now, read the room and see if they’re gonna sit for a while (StockX is a good resource for this). If so, have the patience to wait for them at outlets or even for sales on the various online platforms.

RB: Wu-Tang is for the children.
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MS: Create boundaries for yourself and always stick to them. If you don’t want to spend $30 over retail? Don’t. Don’t chase hype — buy what you like. If you think it looks cool, guess what? It probably does. Don’t worry about if you’ve seen it on Instagram or not.
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NB: This is going to be incredibly corny but I became obsessed with getting new sneakers to be more bold in my style, and match my look closer to my at-times too-loud personality. But in general the coolest part has been the friendships and connections I’ve made with people just bonding over sneakers. It’s such a cool world to try and dive into and the people working in and around the space are some of the most genuinely cool people I’ve ever met. Follow their stuff and support their content because a lot of those brilliant men and women were doing this way before the rest of us caught on to how much fun it is to be obsessed with kicks to an unhealthy degree.
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WH: (Ed. note: Will didn’t have anything extra to add, but insisted that this masterpiece of a photograph of himself be included.)

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MT: You don’t have to buy every release. Let the type of sneaker speak to your personal aesthetic/brand before pulling the trigger on a purchase you’ll regret the day it arrives at the crib. Lastly, if the kicks make YOU happy, don’t let anyone else tell you otherwise.