Five Fits With: Mitchell S. Jackson, Author of 'Fly: The Big Book of Basketball Fashion'

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Readers of the Five Fits With series, I present to you my first subject with a Pulitzer Prize and a TED talk. Mitchell Jackson is an American author of books and countless articles, some of which have appeared in this very publication (also, in the New York Times Magazine, Time, The New Yorker, theParis Review, and plenty more prestigious institutions). His new book Fly: The Big Book of Basketball Fashion just hit shelves and explores deeper themes of race, culture, and economics—and features hundreds of incredibly rich photographs to support the text.

It was fascinating to get his perspectives on fashion and style, and how those things interact with class and race in America. The man is a bona fide clothes-wearer, and one of my recent favorite colloquialisms comes to mind: “He got that shit on, though.”

Beyond the NBA, the accolades, and the fresh outfits, Jackson and I discussed how he found literature and writing, what makes his new book special, how class structure affected his “eye for luxury,” and a whole lot more.

Fit One

Tell me about your upbringing and your path to writing. What prompted you to pursue a career as a writer?

I grew up in Portland, Oregon. I had teachers who told me I was good at writing, but I never took it seriously. I didn't read—I read for school, but I wasn't a recreational reader, and I didn't really think about writing until I was in prison. [Jackson did 16 months in his youth on gun- and drug-related charges.] I was 21 years old before I actually thought about writing as anything other than a homework assignment. When I came home from prison and I went back to school, I started teaching, but a part of the reason why I started teaching is because they didn't used to ask for your record. So really, the writing and teaching are really one thing to me, because I've always been teaching writing, which has always helped my writing, too.

Your new book, Fly: The Big Book of Basketball Fashion, just released. Why did you choose to write about this topic?

I've loved fashion since I was a kid, really. You look at old pictures of me, there are some where I’m in a cowboy hat with buckles. Or a Michael Jackson Thriller jacket and pleather pants, or polo shirts, or Izod shirts. When I reached middle school, I had uncles who were really fashionistos. They would always go to the boutique stores and have all the fly clothes. I had an uncle who collected Esquire and GQ, and he had them in stacks as tall as me in his closet. I always used to go and look through them. Meanwhile, I started playing basketball when I was 10 years old. Those were two constants in my life. I played through junior college, so I was in my early twenties, but I lived around it after. A couple friends were in the NBA, so basketball, probably into my thirties, was also a really integral part of my life. When they brought this project to me, it just made sense. Obviously, I was paying attention to what they were doing with the tunnel and the young guys who were really pushing fashion. It just made sense to me.

Fit Two

How, and in what ways did you surface new information the average NBA fan might not be attuned to?

What's special about this book is that it's not necessarily about the basketball, but the inception of basketball. I don't know if people know about where it started. Everybody knows [James] Naismith's name, but do they really know that they were in there, damn near playing rugby with a basketball? What's interesting about the book is the eras. When we first started, I was going to write it by decades. But the editor said, "No, decades are too arbitrary. We should think of eras." That meant I had to define each era, which meant I had to research what was happening historically, socially, religiously—all of those things to define what the people were wearing. For me, that was the really interesting part, trying to figure out why the NBA players were all wearing the same kind of suit at the inception of the league. Why were they more flamboyant in the 1970s? Why did everybody dress like Jordan? If you're just a casual basketball fan, you might not be a historian. You don't necessarily know about Reaganomics, or that we had clothing conservation mandates in the 1940s in America. To me, that's really interesting.

You started to touch on it already, but when did you first become interested in fashion and what drew you to it?

On top of what I mentioned, it was class. There's this thing now, “quiet luxury,” that everyone's talking about, which is not really a new thing. In the same way, wealthy people don't talk about money. They don't wear clothes that are very flagrant, but people that don't have money have always worn clothes that announced, really, their poverty, right? I grew up poor, and so I was always looking for a way to mediate that, and I did it with fashion. If I had a hundred dollars, I was going to go get the Jordans. As I grew, and got better jobs, and had a little more success, I think I’ve always pushed right at what was comfortable for me. I think I have an eye for what I think is luxury. It doesn't necessarily have to do with price. It has to do with fabrication or fit. Texture. I'll see two things and then I'll go, "Man, I really like this thing right here." And then, I'll look and it'll be the more expensive thing, usually. I've been like that for as long as I can remember. The way I dress is part of my ambition, and that comes from me being impoverished and wanting to, in some way, mediate that poverty with something that made me feel better in the world.

Fit Three

I read an article you wrote for Esquire about baseball and its lack of Black representation. How do you feel the fashion industry is representation of Black folks or lack thereof?

Well, I think the fashion industry is much more diverse than baseball. But, what I also think is that the European brands don't really value Black humanity. I don't want to make that a blanket statement, but every couple of years, I see a major house do something really flagrant that is really racist. Remember Balenciaga and the black face? Or they'll do something with Native Americans. It's like, how are you all still making these mistakes in 2021, or 2023? If something makes an ad or a fashion show, think of how many people had to sign off on that in the company. How many top VPs and presidents have to sign off? To me, that means a lot of people in that company either don't understand the humanity outside of Whiteness and affluence, or they don't care. So I see that. But then you also have someone like Pharrell, or you have someone Virgil, or even Kanye... Or even before them, Karl Kani, and FUBU, like, all those guys who kind of pushed their way through into fashion. But I would say that the European heritage brands still don't want us there. They're okay with taking our dollars, up to a point, but I don't necessarily think they value the humanity of Blackness, in the way that I would hope they did.

Do you think that hiring a Pharrell or a Virgil is…

Like, cover for their racism?

Or, do you think it's just on actual merit? With Virgil, he was doing something special, and Louis Vuitton was the first to be like, "We're getting in on this."

It's not like they're giving an up-and-comer this job. Pharrell is a proven entity. He's a proven designer. He has the relationships he has. I think Virgil was kind of a test case. "We'll give this cool guy a chance and see what he does." And he made good on it. It was a much easier job for Kanye. If we look beyond celebrities, which Black people are getting those jobs? Who's getting that job that's coming out of FIT and studying under Givenchy? I'm sure those people exist, I’m just not as aware of them. That would be more of an indication of what they thought, versus giving a worldwide celebrity a position because he's good and he's well-known.

Fit Four

What does personal style mean to you, and how have you honed yours over the years?

I think of personal style in the same way that I think of writing. I'm not a poet, but I love poetry. I probably love it more than I love prose. One of the things that a poet does is write in form. A form, to me, is a constraint. With fashion, my color palette is really simple. It's like, black and gray, and a little bit of white, and every once in a while, it's a pop of red or yellow. But usually, it's just black and gray. That forces me, when I'm looking for clothes, to figure out how many ways I can execute that. Can I execute it with texture? Can I execute it with fit? Can I execute it with layering? That makes me more creative.

One thing about my writing, if you look at it, I never start a sentence with "I." If you go back and look at anything I've written, 98 percent of what I write does not have "I" in the front. That's a constraint that I give myself, but it also produces a different kind of sentence. My personal style is like giving myself those limitations, but they also are connected to my identity. I don't want to be the most flamboyant person in the room. I like having a sense of something that's special, but I don't need everybody to look at me. For me to be able to have these constraints and then be able to do something that's tasteful, that's really, really important to me. It has to be tasteful, no matter what it is. If your fashion doesn't reflect your identity, you look crazy and you feel crazy out in the world. A stylist can give somebody something that doesn't reflect who they are and they're going to feel uncomfortable. I’ve felt uncomfortable, but that discomfort came from me trying something that's outside a reflection of who I am.

Fit Five

Is there an item in your closet that's most meaningful to you?

It's not necessarily in my closet, but that gold Rolex is meaningful. I purchased it when I signed my last book deal. I had such shitty book deals before, and I finally got the kind of book deal that I always thought I was going to get [when I first started]. You know, when you have these big dreams of, "I'm going to do this and do that," and they're like, "No, actually you're not going to do this." So, when I did that, I said, I'm going to do one nice thing for myself. When I was young, when I was selling [drugs], all the drug dealers had a gold Rolex. The businessmen had them, too. It just felt like a grown person's purchase. Something that I can pass down to my son, too.

If you had the wear one outfit for the rest of your life, what would it consist of?

Really comfortable black sneakers. Man, I'm old. I need some comfort. Some black, nylon pants, because they're probably not going to look old very soon. And a heather gray hoodie.

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