“You here for Gunn?” a towering security guard in a Griselda snapback growls. When his request is confirmed, he nods and opens the door of a pitch-black SUV, and Westside Gunn pops out to make his way into HBX New York. The Griselda general’s reputation — one based on snarling wordplay, dark tales of life in Buffalo and memorable ad-libs — precedes him, but in person he’s charming and good-natured. His security guards notwithstanding, he’s rolling solo with no publicist or crew, and, even though he was given the full scope of Sole Mates only five minutes prior, he’s ready to rock.

When asked what shoe he’d like to discuss, Westside Gunn doesn’t hesitate. “Let’s talk about the Air Force 1” he replies. The Bruce Killgore-designed masterpiece is no stranger to a Sole Mates spotlight, but the Buffalo-born rapper has a slightly different perspective on it, both as a fan and as an artist who sees it as yet another canvas to express himself. He began wearing the Air Force 1 heavily in high school after mostly wearing Air Jordans when he was younger (his beloved aunt Michelle always made sure he had a fresh pair on his feet), and quickly saw it as more than just a fly pair of sneakers to rock to school. Well before his rap career took off, Gunn was involved in clothing design and created custom “Flygod” Air Force 1s with python straps and swooshes inspired by the work of Don C, who he notes as one of his favorite designers.

A lot may have changed for Westside Gunn since those days, but his love of the Air Force 1 hasn’t. In fact, it may be stronger than ever. “Rappers can’t say they’re the best-dressed if they have a stylist,” he laughs. And, as far as he sees it, when you can rock a shoe like the Air Force 1 you don’t need a stylist.

Who or what got you into sneakers?

My aunt Michelle who raised me, rest in peace. She was always very fashion-forward, and though she was my aunt we had more of a brother-sister relationship because she wasn’t that much older than me. She was popular, always had a lot of fly sh*t and always wanted to make sure that I was fly too. The first pair of nice sneakers I ever had was the Air Jordan 6 “Black Infrared,” the very first pair from ’91. I’ve been in this! [laughs raucously].

Was your aunt a big Jordan fan?

It wasn’t even so much that as it was that Air Jordans were the hottest shoes out, and she wanted to make sure her nephew had the hottest shoes. When you get a pair like those “Infrared” 6s, there’s no turning back. You’ve gotta let a kid be a kid, let them enjoy stuff like light-up Spider-Man shoes, but when you put them in that first pair of Jordans, you’ve gotta know it’s gonna start a whole new thing. By the time I was in middle school, I was skipping school to go get Jordans — then I’d show up with whatever the latest drop was the very next day. It wasn’t till I was a senior that they moved the releases back to Saturday so kids wouldn’t do that anymore.

“The Air Force 1 is the ultimate East Coast shoe, as far as I see it.”

So when did the Air Force 1 enter the picture for you? Was it around that same time, or later?

I began rocking Air Force 1s heavy when I started high school. I’d be wearing them sh*ts almost every day. They were definitely big in Buffalo [Westside Gunn’s hometown], and that influence came up from New York City. The Air Force 1 is the ultimate East Coast shoe, as far as I see it.

What were you wearing back then? Highs, Lows … Mids, even?

It’s crazy because now you probably couldn’t even pay me to wear a pair of Mids, but back then it was still cool. You had a lot of options with that strap: you could let it hang loose, or some people would tie their shoestring through it and pull it over. But as the years go by, we’re all like “what were we thinking?” [laughs].

Did you, Conway [the Machine] and Benny [the Butcher] have a friendly sneaker rivalry growing up, or was it more of an “everybody eats together” situation?

The thing about it was that we never all wore the same size, so we couldn’t share. I’d have most of my sneaker wars with my cousin Ock. We’d see who could go the longest without repeating a shoe.

Do you miss how the sneaker game was back then?

The quality of the shoes were better and the designer were better. I felt like brands put more into the product and less into the marketing then, where it’s the other way around now. I’m not knocking today’s sneaker game, because there are some great things about it, but they’re just making so much nowadays where back then it was like [holds hands close together] back then. It was a bit simpler.

It also seems like a shoe’s story was told in large part by the people who bought it and how they interpreted it back then, where today brands give you a shoe with a fully-formed story, leaving less room for a community to establish their own narrative.

For real. Another thing that’s different is that the athlete’s shoe mattered more back then. You’d have a Bruce Smith, a Grant Hill, a damn Jerry Stackhouse, and if you were a fan of that athlete you had to have that shoe. No disrespect to any current athletes, but nobody’s rushing to get the latest signature basketball shoe nowadays.

Do you think that might have to do with how different access is nowadays? Back then, having a signature shoe was a way to feel connected to your favorite athlete, where today you can just follow them on social media.

That’s definitely got something to do with it. The game has changed a lot.

“I’d get Air Force 1 Highs, take the strap off and replace it with a python strap, swap out the standard Swooshes for python Swooshes.”

So you were wearing a lot of Air Force 1s back in high school. When did your interest in customizing your shoes and creating your own takes on the AF1 start?

Honestly, that started before I was into Air Force 1s. I was doing Clarks Wallabees, in the ‘90s, and as the Griselda record label grew I wanted to make sure there was a fashion component to what we were doing, because Griselda was a fashion line before it was a record label and I was a designer before I was a rapper.

I decided to work with python, so I’d get Air Force 1 Highs, take the strap off and replace it with a python strap, swap out the standard swooshes for python swooshes, and those were the Flygod Air Force 1s, which I made like 50 pairs of. Eventually, I started doing Air Force 1 Lows, where instead of swapping out both Swooshes I’d just do the inside ones. I love making stuff like that, man. At my listening party last night, I saw someone with one of those original pairs and it made me smile, ‘cause I was like “damn, you’re one of those 50 people that got a pair.” It connects me to the fans.

What made you pick snakeskin as your material of choice?

I was inspired by Don C. I’m a huge fan of his work — his first Air Jordan 2 collaboration is my favorite shoe of all time — and I collect his python hats as well. I honestly started working with snakeskin because I wanted something crazy to match my hats.

You must have a lot of creative freedom working that way. Do you prefer to have that full creative freedom as opposed to, say, partnering with a brand, or would you be willing to do that if that opportunity came around?

The thing about it is that when I’m doing it myself, I feel like what I’m making are art pieces, not sneakers. I’d love to do something with a shoe company, and have already been tapped on the shoulder once or twice, but I’m not in any rush — I just want it to happen organically. We’re just havin’ fun, man.

Talk to me about bridging the gap between the Air Force 1, a classic street sneaker, with high-end sneakers, which you also love. How do you find that middle ground between the two without leaning too heavily one way or the other?

One thing about me, man, I love to cater to everybody — even with the music. That’s why if you come to one of my shows you’ll see a 10-year-old kid waiting in line with his grandmother to get mercy, then behind them is a 45-year-old who’s like “man, I didn’t love hip-hop for a decade before you came out!” I don’t want to be put in that box, and I don’t want my shoes to either. Maybe they were $100 retail, but now it’s $500 retail thanks to those exotic materials. It’s the best of both worlds.

And that’s an interesting middle ground to touch, because a lot of designer shoes can’t become a classic in the way that an Air Force 1 does because they just don’t age well, unless it’s something like an America’s Cup.

Correct. And the Air Force 1 is a great shoe to do that with because it’s an easy shoe to reconstruct. I don’t know how it would have gone if I’d have taken that route with a New Balance [laughs]. The Air Force 1 is like a blank canvas, and I think that’s why people will go so crazy with it.

If you made the ultimate Westside Gunn Air Force 1, what would it look like?

The whole shoe would be python. Official! Real python, with a silver tone and a red suede check. I’d be coming with the crazy thick python scales — there’s a certain part of the snake that has these textured scales you can see from a mile away. Even python shoelaces.

The question begs asking: do you like the Air Python?

I really don’t [laughs]. There’s nothing wrong with them though, it’s just …

Levels?

Levels. My ultimate Air Force 1, with the full python skin build, that’s not something that you could sell at retail because it’s too expensive and too hard to make. Sure, I could hit up Shoe Surgeon and we could work on that crazy Flygod sneaker, but if Nike were to hit me for a collab and I wanted to do something with snakeskin, it would have to be more [mass-market], so I understand why a shoe like the Air Python exists.

How would you say your perspective on the Air Force 1 and on sneakers as a whole has shifted over the years?

I’ve just seen the culture grow and shift so much, man. That’s why you can have a shoe like a VLONE Air Force 1 come out, or something like a Terror Squad or Roc-A-Fella Air Force 1 get a full retail release. Those shoes come from hip-hop and they had the streets on fire. And that’s how I hope mine will be when I get that call. Notice I said “when.” [laughs].

Before we get out of here here, we’d be remiss to not talk about one of your other passions: wrestling. If you were put in a tag team TLC match during the Attitude Era, who would your partner be and what shoes would you wear?

[long pause, chuckle] Woahhhh. My partner? Attitude Era? Chris Jericho, and … we’d probably be … ehhhhhhh … man, what would we be wearing? What would Chris do? Shouts out to Chris man, Y2J and all that. We’d probably have to go Sheed Air Force 1s, cause we’re wrestlin’ and we need that support. Give us those high-top black patent leather joints, or maybe the Riccardo Tisci ones, the ultra-high joints with the big check.

And finally, why are sneakers important to you?

Personality, man. Sneakers show your personality. You can wear anything on your body, but that shoe? That shoe is everything. You could see someone walk in here right now with sweatpants that look like they’ve been rocked for four days straight and a beat-up hoodie, but if they have on some Chunky Dunkys, you’re still gonna be like “Oh, sh*t!” It changes everything. The shoe is everything. And I’m Flygod man, this is what I do. It’s always about the shoe.