Dapper Dan Gives You Permission to Wear a Hoodie

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Dapper Dan wearing his Gap "Dap" hoodie
Zoey Grossman for Gap

Apart from a full-on sweatsuit, the last thing you’d ever see Dapper Dan—the legendary, hugely influential, and ever immaculately dressed Harlem-based designer—wearing is a hoodie. And yet, that’s exactly what he chose to design when Gap approached him to collaborate. The 77-year-old is hoping it’ll serve as something akin to a gateway drug, opening the eyes of the young folks (whom he always has his eye on) to ascots and more of the “throwbacks” that comprise his wardrobe staples. As the many, many, many Harlem residents who stop him every single time he steps out of his Ralph Lauren-inspired townhouse will tell you, the aptly named Dapper Dan (born Daniel Day) is never not dressed to the nines.

Then again, the fact that Day went with something so prominently emblazoned with the “GAP” logo—in this case modified to read “DAP”—is no surprise. He pioneered logomania as we know it today, making such an impact that a few years ago, Alessandro Michele infamously mimicked one of his decades-old designs. Day has the opposite of hard feelings, and why shouldn’t he? As he puts it to W, Gucci and Gap are among those “who’ve been dying to have something associated with me directly,” and he’s returned the love by making their clothing the only items in his wardrobe he hasn’t designed himself.

What’s your first memory associated with Gap?

LL Cool J. I have minor memories, but none that I can pull up with as much intensity as when he did that rap in his campaign [in 1999]. It was amazing—Gap is the great American company, the great American brand, and to have LL come on with rap…? He was like the Pat Boone of his generation—someone who could introduce something to a larger audience. That’s what LL Cool J did: Gap is mainstream America, so he brought rap to mainstream.

I would have said Telfar, but since his Gap collab very sadly fell through, maybe Kanye would be a good equivalent?

Maybe Kanye would be the modern version. What Kanye did for Gap is so amazing. He gave all of us the opportunity to have something on our backs that’s connected with the elite, but suitable for the average American. I hope I can do that as well.

Why, of all things, a hoodie?

I like to elevate, so I encourage young people to dress up. What they call, I don’t know, streetwear, is really expensive, and it leans away from the generation that I came up in. That suit look is so sophisticated, so I said, how can I bring them closer to that degree of sophistication? I don’t wear suits [anymore]—I try to wear a lot of vest outfits; you see my [matching] pants and vest now. And I make the pocket square match the shirt or the ascot. So when Gap came along and gave me the opportunity to do something different, you’ll see in the campaign that I’m wearing a hoodie with an ascot. I’m bringing the younger man upstairs, you know what I'm saying? Letting them know that we can be sophisticated no matter what we wear.

Do you have a sense of how many pocket squares and ascots you have?

No, I don’t. I do know I need more space for ‘em.

The hoodie only comes in one color—a rather uncommon shade of salmon.

I love when parents are walking with their children and they point at me. I use the colors to attract young people. One of my favorite things I do is when they come by and have on, like, an exciting sweatshirt, I ask ‘em what’s going on on their back. They almost pull a shade around to see. And then even if you go beyond that, I ask if they know what the symbol [they’re wearing] means, just to see what it was that made them even buy it. And what I’ve discovered is that color is the no. 1 attraction. Everybody who’s responded to my Instagram [about the Gap collab], all they keep talking about is the color.

Is there a young person whose style you particularly admire?

There's a young guy, Walter Harvin, I was introduced to the other day. He’s what in fashion I call a “boy wonder”—let me explain to you what that is. A boy wonder is a younger guy who’s part of a generation that, everybody likes the way they dress, and he’s an influence on all of them, although he’s not a big star. And Walter is one of the guys I’m excited about. Just on style alone, he’s generated a following. Not from people who post up—people gravitate toward him for his style alone. But my no. 1 guy right now, today? A$AP Rocky. Because any time you can stay in the space you in… you stand there with a pocketbook, and you come from Harlem? That’s huge.

Have you seen any of Rihanna's maternity style?

Yeah, I love what she’s doing. I like Ashley Graham as well—I think they bring something to that. But Rihanna, I think she takes it to another level, a higher level.

What was the last fashion item you purchased?

Oh, I don’t… being Dapper Dan and being in Harlem, the worst thing I could do is be in the club and somebody got on the same thing.

How often does that happen—or has that ever happened?

No. That’s like shooting myself in the foot trying to shoot somebody else. I can’t do that, you know? I see a lot of things I like and I say, “Damn. Nah, I know somebody gonna pop up with that, and that’d destroy me.” All the outfits that you see me in, if I didn’t get them directly from the Gucci store, then I made ’em. That includes what I'm wearing right now. But I will be adding The Gap to the bag. Need the Dap to augment the Gap, you know? The problem is, I gotta get dressed to go to the store, because people expect to see me looking a certain kind of way. So I have the outfits already laid out, you know. Shoes, everything figured out.

How far in advance do you plan?

It depends on what my itinerary looks like. If I don’t have anything going on, I like to have two or three days on average. But if I know I got a big schedule ahead of me, I just keep lining them up, with some [additional] options based on the weather.

When was the last time you hoped no one saw you because you knew you weren’t at the top of your game?

That happens all the time. As I tell everybody, I do not dictate fashion—I translate culture. To tell you what I do, and what excites me so much, I would have to tell you a Harlem story. Being born and raised in Harlem, a diverse section of East Harlem, I had Italian friends, Irish friends, Greek friends. I've seen and witnessed a lot of people and culture, and I like to see and embrace what each person brings to the culture. A lot of African Americans, especially young people, don’t understand the heavy impact that Italians living in Harlem had. The gangster element—the John Gottis and Al Pacinos—all the gangsters had a heavy impact on fashion.

So before the pandemic, on Friday nights, I would hang out in Puerto Rican clubs and embrace their style, which tends to be a little more conservative for Puerto Ricans who are born and raised in New York. And then on Saturday nights I would go to the Dominican club, where they push the envelope more. I used to go downtown just to see what they’re wearing in different communities. That’s how I get a take on how I should put things together. So the outfit I wear in a Dominican club, I would never wear in a Puerto Rican club because—it don't fit. Have I ever been caught in the wrong outfit in the wrong place? Yes, I have. [Like] I thought I was going to a Dominican club and ended up in a Puerto Rican club, they say, “Damn, what’s wrong with him today?” [Laughs.]

Apart from your own store, where would you recommend people go shopping in Harlem?

I would only recommend stores that have that shift going on.

What do you mean by “that shift”?

They allow people to be different. Harlem Haberdashery still makes couture, so I would recommend Harlem Haberdashery. They’re the only ones beside myself that I know of right now doing couture on a regular basis.

What’s the most prized possession in your closet?

I haven’t even worn them yet—and I’ve had them for six or eight months—but I have a pair of crocodile loafers from Gucci that cost $5,400. My friends are asking me just to take pictures of ‘em, so I just take pictures of ‘em and send them. Crocodile and alligator have always been staple items if you want to be really part of the elite dressing circles in Harlem, all the way back up to yesterday. I crossed over from alligator, crocodile, silks, furs, that kind of thing—what allowed me to move into a higher level was logomania. It has the same prestige as those materials, but allows you more variation, more creative space to work in.

I'm so curious what you dressed like as a teenager.

Like an older man, because I didn't want to be a teenager. We had two styles growing up: One was called prep or rugby style, and the other one was called hustle style. But can I tell you one more story?

Please do.

In this very room right here—after, you know, the big thing with Gucci appropriating my style—by that table in the back, Alessandro Michele was here. People had been telling me he said this, but I had to hear it for myself. He said, “I don't know why people didn’t get it. I was not appropriating you—I was paying homage to you.” And here’s why: He said he saw a video of me in my boutique on 125th Street dressing LL Cool J. LL had on one of my outfits, and I had on a suit and tie, which is what I used to wear back in the day a lot. [Michele said that when he] saw that picture, it changed the whole world for him. He said, “I could see that people could be different and still do things, you know?” You see, at the time—we're talking 30 years ago—it was a big deal to be gay in Italy. That’s the story he told, and it’s a story that gave me so much more depth to what I was doing. I felt, Damn, I never knew that I could inspire him—somebody who’s reached the heights that he has today.

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