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Dapper Dan Thinks Kanye West Is Doing It Wrong

One of the most compelling aspects of the talk I had with Dapper Dan was what he had to say about Kanye. The conversation put on display how different their respective generations' approaches are to realizing their creative dreams.

I met Daniel “Dapper Dan” Day in early January at his regal brownstone in Harlem, a few blocks from 125th Street. The brown-skinned sexagenarian jogged down his grand wooden staircase and greeted me with a stiff dap. Dan sported a wide-collared Hawaiian print shirt with oversize octagonal gold buttons and matching rust-colored lamb’s-leather vest and pants—all of which were his design.

If you don’t know, Dapper Dan was a hustler who became a fashion legend in the 80s for making bespoke menswear garments at his eponymous boutique in Harlem for black celebrities like Mike Tyson and crack kingpins like Alberto “Alpo” Martinez. His clothes were emblazoned with the monograms of European fashion houses at a time when those companies—Gucci, Louis Vuitton—were mainly producing leather goods and accessories. Eventually, when the fashion houses realized what Dap was doing, they sued him out of business. Even though his boutique was short-lived, the flashy leather and fur sportswear he crafted for the black elite was way ahead of its time and became a pivotal influence on men’s fashion and the aesthetics of hip-hop culture.


I came to Dapper Dan’s home to talk with him about the topic of black masculinity through fashion for a feature that ran earlier this month, in VICE’s annual fashion issue. The conversation I had with Dapper Dan for the piece was long and unwieldy. It covered tons of history, as well as a lot of Dapper Dan’s own personal story. Although I’m extremely proud of the published piece, there was a lot jewels from Dap that just didn’t fit. Considering that, I felt obliged to give you guys a more extensive version of the interview I had with him.

One of the most compelling aspects of our talk was what he had to say about Kanye. At the time this interview took place, 'Ye had just scored his new sneaker and fashion-range deal with Adidas after complaining about his previous deal with Nike in a series of high-profile interviews. My talk with Dapper Dan about Kanye put on display how different their approaches were to realizing their fashion dreams. Dan tried to rail against the machine by making illegal, priceless garments. Kanye, on the other hand, is trying to become one with the machine and remake it in his own image by working with major brands like Adidas. Only time will tell if it will all work out for Yeezy—but, for what it's worth, I think he's on the right track to making history. Dan isn't so sure, however. And maybe that says something about both of us and our respective generations. Or maybe not. Who knows? One thing I am sure of is that this Q&A should give you a good idea of the vast knowledge and history that Dap can bring to discussions on issues of race, masculinity, and fashion. Hopefully, it won't be the last time I get to pick his brain on these topics.


VICE: Let’s talk about masculinity.
Daniel “Dapper Dan” Day: Masculinity is something that stayed on my mind as I grew up in the ghetto. My whole life, manhood was the only thing that we could truly look forward to. We couldn’t look forward to having money. You know what I mean?

How’d you know what being a “man” was?
As a kid, I was surrounded by my older brothers, my cousins, my uncle, and all these street guys. And I was raised by my father. So there was an idea of manhood that was drilled into my head at a young age. But my personal concept of manhood I had to develop on my own.

How did that start?
Well, the most profound statement a guy ever made to me about this… I can’t give you all the circumstances under which he told this to me. I’ll just say I was in a terrible situation when I was 18 or 19, and he was in the same situation. We were battling this psychological thing. And he said to me, “There’s two kinds of men: One is a man among women and the other is a man among men… Always strive to be a man among men.” That always stuck in my head.

What does that mean?
The way your personality plays out in the group that you hang with determines your place. On the street, you don’t find out who you are until that split second when you have to make a decision. For me, it was when guys tried to kidnap me and shot me in the back.

Whoa. What happened?
The guy told me, “Get in the back of the van and lay down.” The other guy who was with me—he went in the back of the van and laid down…


The older guys always told me that there comes that moment when you have to do certain things in your life. Prior to that, I had made a decision when I went into the street that I didn’t care if I died, because you cannot make it in the street unless you have that feeling. Guys get that feeling through drugs and getting high… But the most dangerous guys I ever met in the streets were the guys who didn’t need the drugs.

Do you think it takes a different sort of masculinity to survive on the streets as opposed to anywhere else?
There are different kinds of masculinity. But to me there’s only one true masculinity, and my father is my emblem of that. He went to work everyday, never missed a day but once in 15 years. And he was only late that day, never absent.

What do his actions represent to you?
You might call it vicarious atonement—like how Jesus died on the cross to save humanity. When you see that sort of thing played out in a person’s personality, that’s what I call masculinity. Being a man is being responsible in life to your family and your community and your country. And if you don’t like something about those things, then be man enough to stand up and change it.

In the streets, why do you think “the gangster” is what a lot of young men want to be?
If you want one sentence: It’s the holes in the shoes. When you’re deprived of everything and you see somebody in your community making it and you don’t have that staircase to go up, but you see someone else doing it a different way, [those gangsters] become your first heroes—especially if you don’t have a father. I was fortunate enough to have a father.


What is it about the gangster lifestyle that is so alluring?
It looks like magic, and it seems instant. The other process seems long and played out… You have to go to school; you have to do this; you have to do that. But when you see guys go out and sell drugs and rob, it’s like instant cash and instant gratification. They are overnight sensations. But they offer this distorted concept of masculinity.

What do you mean?
Look at all the gangsters: They all started telling when they got caught. Real masculinity is not being able to inflict pain but being able to take it. And all of those gangsters, as soon as they got busted, they flipped the script.

Speaking of gangsters, what was the crack era like for you in Harlem?
Crack flipped me out. There was a crack house four or five buildings down from my store. The people I saw going in there… I could not believe it. I’d see decent-looking people go in there before work and get their lives destroyed. The drug situation in Harlem was like what you see in Brazil in the favelas. The police didn’t even bother.

How have you seen the approach to masculinity for black men change over time?
Everybody has this concept that all black people in America are pretty much the same. No. We’re tribal. So masculinity might be defined in different ways in different parts of the country. But if you want me to address it as far as Harlem is concerned, I can do that.


Is there anything that makes today different than before in terms of masculinity in Harlem?
Back in the day, the Five Percenters, the Nation of Islam, and other militant black groups defined masculinity. If you were caught outside of their zone, you wouldn’t feel comfortable. So that had a heavy impact on us. Even guys who were not involved in the revolutionary cause would feel uncomfortable if they were not dressed a certain way. It was ironic, because the light-skinned blacks who were always considered uppity went out and got the biggest afros so they didn’t feel like outsiders. And then, when you look around, you’d see that some of the most militant blacks were light-skinned, like Malcolm. You have to remember that the Nation of Islam was recruiting guys straight out of jail, so that’s a powerful influence. Whereas the Panthers had more of an impact on people who were politically conscious and knew how governments work. The Panthers were reaching the college students as opposed to the street guys.

How do you think Obama has impacted the way men dress and carry themselves?
As far as the street is concerned, Obama’s election was like a concert. All around election time, people were wearing the T-shirts, buttons, and all that kind of crap. But to say that it kicked in a certain style? No. A certain feeling? Hell yeah. I’ve never seen so many black people at the election polls in my life. It was like the Million Man March. But did it change how black men carry themselves? I don’t think so.


Photo via Wikipedia.

What do you think about Kanye and his impact?
Kanye is making a mistake. He is begging and waiting for somebody. To people like me who struggled, he’s an embarrassment. He’s got all this money, and he’s knocking on the door. I was dead broke. I told my friends back then, if they weren’t going to let me in the door, I’ll just do what they do better than they do it. And do it for us.

I think the reason he’s looking for support from big corporations is because he wants to do his thing on a massive scale, one that can’t be achieved without the support of players like Adidas or Nike.
He admitted that he’s an artist, but he doesn’t know how to sell his stuff to the public. That’s his problem. I don’t think he’s in touch. Does he know what excites the people on the street? Or is it just that he wants people to wear something because he’s wearing it? He should study why black designers before him didn’t make it. If he had done that, he would have known what to expect.

If you could talk to Kanye, what would you say?
“Let’s take this little bit of money here and put it over here in a fashion business. They won’t even know it’s us. Let’s nurture it a certain way so we can see how the game goes.” If he comes out with a line with his name on it and fails, then he’s branded a failure. When I was making clothes, people would come to me and I’d say, “No, no. They’re going to control me. They’re going to do it the way they want to do." I’d rather not come out until I can control the elements in the game as opposed to experimenting with my own name. You don’t get a second chance. Not on his level.


The biggest downfall with your business was getting sued by a lot of big fashion companies. Now they’re doing stuff that is so similar to what you did back in the day. How does that feel?
I feel like, Yeah, sucka. [laughs] And you know what? The real impact hasn’t hit yet until all the young people know. When all the young people know, then I’ll feel like, OK, y’all thought we couldn’t do this, and now y’all are copying me.

Who do you think bit you off the most?
The other guys, you can understand. They were established already. But Tommy Hilfiger, his whole style was off our backs. The other guys were already in business. All they had to do was change a little. Tommy Hilfiger, he came in with the whole nine. His whole platform began when he started sending his brother Andy to rap clubs. So he built everything on that. I pick up the paper and I think, Oh ,God, if I was white…

Can you talk about how your story would be different if you were white?
If I was white? Oh, man, I didn’t have to be all the way white; I could have been Jewish… I would have had a clique. [laughs] The only thing that ever held me back was… Actually, my color didn’t even hold me back. My perception of my color held me back. Reverse prejudice held me back. If I had been more open to dealing with white people and Jewish people, I would have been more successful today. Back in the day I stayed angry, and I didn’t even realize how angry I was. But anyway, that’s my problem. That’s why I’m so happy about my son. He’s growing up in a different world.


Do you think the same limitations are there today for a young black man that were there when you were growing up?
No. First of all, the white guys coming up today are different. The large majority of them are not like their parents. They just have that subliminal prejudice; they don’t even know they’re prejudiced. And some of them have even overcome that! And a lot of the young black guys coming up, they’re not as angry as I was and as distrusting as I was of white people. So it’s a big difference now.

Why do you think you were so angry?
I got tricked. I have to admit it. I got tricked in the sense that those demagogues who needed us to think that the white man was such a devil exploited us to the point where it stunted our growth. I’ve seen guys where it had a more detrimental effect on them than it had on me.

Who would you say those demagogues are?
I’m not going to call out any names. Don’t start that. Are you trying to get me killed? [laughs] But trust me: I know who it is. I tell my children and my grandchildren who they are and to keep their eyes open because people make money off of you believing certain things about other people.

Do you think that has anything to do with Kanye’s perception? Maybe he has learned from stories like yours and he realizes he can’t do it himself, so he’s reaching out to those corporations to realize his dreams.
I think my expectations of what the white power structure would allow me to do was completely opposite to what his expectations are. He expects to get in the door. I expected not to get in the door. His problem is that his expectations are too high.

What’s the sweet spot then?
Russell Simmons, because he hit the right blend. Russell Simmons is a master because he hooked up with that Jewish guy and that was it. That gave him the balance that I didn’t have… I will never allow myself to limit myself to people like myself, again. There’s no growth in that. If you’re white and you don’t have any black friends, you’re missing out. And vice versa. You’re limiting yourself. You need to be gay, straight, white, black, Spanish, English, everything. The more people you come into contact with, the more growth you’re capable of. And I needed to know that when I was younger. I didn’t have anybody to tell me that. All I had were the people who were saying, “Don’t let that white man do that. Watch out.”

It’s different now, though?
My son now doesn’t have to worry about those issues. I don’t want to make him like me. I don’t want him to be like me. I want him to be himself in his own world and just snatch pieces off me and do his thing. It’s more fun for me to see how it all plays itself out.

A lot of dads try to mold their sons in their own image. What stopped you?
It was this one time his cousin was over at our house. And I didn’t like the way his cousin was talking to him, and I wanted him to beat his cousin up. But that’s me; that ain’t him. I wanted him to kick his cousin's ass. And then, his mom was like, “Uh-uh, I don’t want anybody in this house that is against this house. Blood or no blood.” I wanted to kill that little bastard. But my son is different. He didn’t grow up like me, angry at everything. That’s the beauty in him.