How Biggie Went From Ashy To Classy: By People Who Styled Him

Biggie Smalls was the illest…Big had a top-notch flow, a booming voice, and lyrics drenched in authenticity and humor. The all-time great MC born Christopher Wallace said it was all a dream, and then he took us on a ride from his time as a stressed-out kid in the streets of Bed-Stuy to when he made that dream a reality by becoming one of the biggest stars on the planet. And he did it all through sheer force of will and talent.

As metamorphic as Big’s life was, his iconic style shape-shifted too. Heads watched Biggie’s fashion transformation play out in real time. In five short years, The Notorious B.I.G. went from wearing bandanas and t-shirts to rocking tailored suits and silk shirts. As Biggie himself said on “Sky’s The Limit,” his style went from “ashy to classy…” And, it turns out, that was by design.

Behind the music videos, the Source magazine covers, and the unforgettable red carpet looks were two people who helped transform Biggie Smalls into Big Poppa. One husband and wife team helped turn a man who described himself as “far from handsome”… and who sewed fake logos on his clothes as a kid…into an international sex symbol whose fashion influence was generational. This is the story of how those two people helped take Biggie from ashy to classy.

Here is a transcript from this interview that has been edited in several places for length:

Ambrosia For Heads: “Taking Biggie from ashy to classy,” [in Sharene Wood’s words]—everyone knows that line, everyone knows the impact, everyone has heard it in his head, but no one has actually seen it or heard the story of how that journey began. So I would love to hear from you all, how you took Biggie from ashy to classy…But first, could you introduce yourself?

Guy Wood, Sr.: I’m Guy Wood. I’m the designer and owner of 5001 Flavors.

Sharene Wood: And I am Sharene Wood. I’m the president and CEO of 5001 Flavors. We just celebrated our 30th year in business [which we founded in] 1992.

Ambrosia For Heads: You’ve worked with artists such as…

Sharene Wood: Biggie Smalls, Heavy D, Puff Daddy, Mary J. Blige, [DJ] Khaled

Guy Wood, Sr.: [Big] Pun, Tupac, No Limit, Swizz Beatz, DMX, The LOX, Justin Combs, everybody…

Sharene Wood: And then, if you want to go into celebrities—not musicians—Lebron James; we definitely do a lot of artists, and entertainers, and athletes.

Ambrosia For Heads: Can you describe to me what Biggie’s fashion was like before you guys met him?

Guy Wood, Sr.: Yeah. Biggie was rough around the edges when we first met. [He might wear a] t-shirt, baggy jeans, and a pair of scuffed-up Timbs. But that’s a no-no in the Hip-Hop world; you wear Timberlands one time. [Laughs] But the beautiful thing of it [was that] he was a student. He would listen; he was a blank canvas. So Puff would come in and interject, “Yo, I want him to be the biggest this, this; that; I want him to look like this.” So I said, “I’m listening to the lyrics…” I said, “Big, you’re talkin’ a lot of stuff on these lyrics. The look has to match what you’re saying. So if you’re talking about ‘My Detroit players wearing pink gators,‘ we gotta get some pink gators. We gotta get Versace-ish shirts, print fabrics. Yo, we gotta take it to the next level.” He’s not scared of color; he cleaned up well. So that was the beauty of it.

So if you notice, in the first video, “Juicy,” he lied about his size. He said, “Oh, I’m a 2X and I’m a 38 pant.” So when I bring the clothes, nothing is really fitting properly. I said, “Big, you cannot lie.” And back then, everything was baggy. It was too tight…he had the slim fit. He said, “Okay. I understand. I’ll let you measure me, and we’ll move forward from here.”

So from that point on, he trusted me and we was able to do our thing. So whenever you saw him, from “Juicy” to “Hypnotize,” was all us. He wasn’t scared to do suits. He wasn’t scared to wear colors. Even when he did his own dates where he’d—it wasn’t just video clothes, he would invest his money in himself and stay fly.

What I loved about him was all his team members, he would get them fly too—get them gators, get them a silk shirt, get them—Lil’ Cease, and Money L, and all these guys that were behind him, people that’s on stage with him, he took care of them.

And everything was a process: I would go locate the shoes. “These are the colors that they have in your size.” Okay, alright, so let’s go with these three looks, and hold those other three colors for next week, or two weeks,” and do that.

And so it was a process. But what I loved about him, he knew—just like [JAY-Z]—they know what the pulse of the people [is]. When he says, “Throw your Rolex in the sky and wave it from side-to-side,“ everybody had to have a Rolex. So every guy ran and got a Rolex; every girl ran and got a Rolex. When he had, “Coogi down to the socks,“ we had to get Coogi socks. So the whole point was, yo, be real. Whatever you sayin’, let’s create this picture—and that’s what it was. It mini vignettes, mini movies.

Ambrosia For Heads: You said that in the beginning, it was “Versace-ish.” What were the budgets like in the beginning?

Guy Wood, Sr.: Well, the budgets were always small. In the very beginning, they were small. Then they got super big.

Ambrosia For Heads: Were you “sewing alligators on the shirts,” or not that small? [Laughs]

Guy Wood, Sr.: Nah, nah. [Laughs] We wasn’t doing that small. I mean, maybe the first budget might have been $1,500 for three looks. That’s small; that’s $500 a look.

Sharene Wood: —And Versace wasn’t making clothes for him. Even though he was [rapping about] Versace, it was Versace print. It was a look that we would make for him and Puff for the videos, supporting [their lyrics].

do. You see what they’re doing Guy; I need something like that. What’s my dress-down look?” We would just always be thinking. I’d see ideas, and I would shoot ‘em by him, and tell him, “This is what I’m thinkin’, this is what I feel.”

And what’s so beautiful, with Biggie, I have the relationship with a few other guys too…because, my clients, they trust me. So it’s like, I put you in something that you feel you comfortable. It’s not my vision; it’s our vision together, so it’s hard to beat that. When I can bring your likeness or [your] idea to fruition. It’s just like you tell your lady or somebody, “This is what you want for dinner,”—and then they make that exact dish, you’re like, “Wow, this is how my grandmother used to make it.” It means something to you. And that’s what I love about the one-on-one, the bespoke that. I can’t think for the masses because I like to think for one person. And if the masses love it, then that’s great. But be true to that one person. That’s all I’m here for; I’m here for you. And if at the end of the day, if they love it? Then guess what, I did my job, and now I’m moving onto the next project.

I can’t even look back over my shoulder and say what I did [recently]. I gotta do something this week, and I gotta do something next week…

Sharene Wood: It’s history. For us it was a job—it was completing a job so we can get a check, but then I think, ultimately, I started to realize, oh, we’re making history. These images become part of a historical time. You can hear music when you look at the picture; it becomes a billboard. It becomes something that’s culturally important and relevant, and in a museum. And then it hit me, okay, oh so we’re not just making checks, we’re making history.

I don’t think any of these young people starting was like, “I’m gonna do this so that in 50 years they’re gonna talk.” People are trying to survive, trying to express themselves, trying to start brands, trying to get some paper. So when I look back at it, I’m like wow, I didn’t really realize that what we were doing was really changing the world. So we started out as urban, and now we’re completely mainstream.

Ambrosia For Heads: You talk about those iconic images. What are a few that you all can remember that people would know from Biggie?

Sharene Wood and Guy Wood Sr: The [July 1995] cover of The Source.

Guy Wood, Sr.: Yeah, that one-piece gas station suit in leather. That was just iconic, ‘cause it had our logo on it. Plus, he had arrived at that point. And then, The Source was like ‘The Bible Of Hip-Hop.” It was like being on Vogue–for us. Now we done did Met Gala, we’re in the Rock & Roll Hall Of Fame with outfits, the Smithsonian, so we’ve done a lot of stuff, but the one that means the most to me is Big, Big’s career— it’s just because I was there from day one. I didn’t latch on at the end—and we’ve done that with a lot of people, but Big—he was just the one. We still rock to his music now.

Ambrosia For Heads: You told me that he lays in rest in your outfits…

Guy Wood, Sr.: Yeah, That was the hardest thing ever, to make an outfit that you have to—and we’ve done that for a few clients, and that’s the hardest thing: picking fabric for somebody that you know this is their last time.

Sharene Wood: I always tell the story: because we didn’t make it for his funeral; he ordered it before he died. Two weeks prior, he ordered a bunch of stuff and said, “I need a white suit.” I was like, aight. It didn’t make any sense, ‘cause he had a white suit from “Hypnotize,” but he didn’t know what buttons he wanted. And so it sat there. And unfortunately, he passed away—and Faith [Evans] called and said, “I need a white suit for Big.” And it was already made because he had ordered it. That was his last order. It so it was predestined; I don’t want to think that. But the fact that he ordered that made no sense to me then. He was like, “I’ma need it in two weeks,” and he needed it. Yeah…I didn’t know that I was gonna talk about that today…

Guy Wood, Sr.: It’s crazy, man. That was hard. That. Pun was hard. Nipsey [Hussle] was hard. These guys—even the Tupac—it was just…like, I know these guys. And it’s like, okay, you’re not agreeing right now. But I know you as a man. He don’t want you to die. He don’t want him to die over this; this is wrestling. This is what I always tell them: this is wrestling, B. You’re picking characters. Don’t get caught up in this. Al Pacino is not…he’s not real. That’s the only thing with us, we get caught up in these characters, and we have to become who we think we are. Nah, you don’t have to. That was a role. Push that back, and the next character, you might be something else. You might be a dad, you might be a pastor, you might be a pilot [in] the next movie or the next video—that’s how I look at life. I don’t sit back and glorify the stuff I’ve done; I keep looking for the next job or the next project, because at the end of the day, that’s done already. That’s history.

You can’t keep looking back over your shoulders. I look at some of the stuff and [forget] I made it. Because I’ve done so much stuff—and that’s not to be bragging. I try to tell that to the young designers that I have around me. Don’t get caught up on what you did last week. Don’t worry that they’re copying what you did last week. You gotta do something new; you can’t keep talkin’ about a bubble-vest that we did 32 years ago.

Sharene Wood: Plus, sometimes, when I bring that stuff out of the archive, it is fascinating. Like, people will be like, “Oh, y’all made that? I remember that!” Above The Rim, Tupac—when he had the red leather baseball jersey, we made that.

If I sit down and really start to think about it, I’m like, I’m impressed. ‘Cause to me, it’s just making an outfit. But it’s not, it’s making stuff that generations will see. And so we’re in movies, award shows, tours, red carpets…and when I start to look at the images, I’m like, our people were out here doing it. Successful, making music, setting trends, motivating markets, making money, [going] all over the world touring. Like, I love to look back, ‘cause I feel like our success is our clients’ success. So we go from obscurity to fame with all of our clients. I’m like, wow, we went along for that ride, ‘cause once people have a look, you become part of their brand because they need that look to continue. And so that is what we have going.

Ambrosia For Heads: So here we are, celebrating 50 years of Hip-Hop history. You are all a part of 30 of those 50 years. What do you want your legacy to be remembered as, when all is said and done?

Guy Wood, Sr.: A person that just loved fashion, loved Hip-Hop, loved the culture, and always wanted to give people quality looks.

Sharene Wood: And so, for me, it’s more of a business legacy. We started with 5001 Flavors, we also have a retail store in Harlem: Harlem Haberdashery—we just celebrated 10 years in business. We have expanded that to HH Bespoke Spirits & Beverages. We have a rum, a gin, and a vodka, and an alkaline water. So for us it’s about brand evolution, it’s about building a business legacy, and it’s about motivating generational wealth in our family, and doing something different. For me, that’s what Hip-Hop is—and I don’t think even Hip-Hop understood how much it could motivate the markets of the world. And so when we talk about like JAY-Z and Puff, we’re talking about multi-industry moguls. And so for us, that’s the legacy that I want to leave—business legacy.

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