How Fashion Picks Its Hip Hop Style Icons

0:08Sheena Butler-Young: Hello and welcome to The Debrief from the Business of Fashion where each week we delve into our most popular BOF professional stories with the correspondents who created them. I'm senior correspondent Sheena Butler-Young.

0:20Takanashi: And I'm executive editor Brian Baskin. Hip-hop is one of fashion's most powerful pipelines into pop culture. From fragrance campaigns to sneaker drops and front row placements, brands have leaned heavily on a small group of superstar artists who mostly came up during the 2010s to drive visibility and relevance.

0:39Sheena Butler-Young: Nobody embodies this trend more than A$AP Rocky, who is undeniably a cultural force. His collabs have run the gamut, from Puma to Ray-Ban to Marine Serre. But as Gen Z grows more disengaged with luxury, and as music charts become less predictive of cultural influence, the industry is being forced to reconsider how it courts hip-hop's biggest and rising stars. BOF correspondent Leigh Takanashi joins us to unpack it all. Leigh, welcome to The Debrief.

1:05Brian Baskin: Thank you, Shina and Brian. I'm so excited to talk about this with you both today. You know, hip-hop's been something I've been actually covering even before I started writing about fashion for BOF. I ended up writing a lot about it for Mass Appeal, Complex, and I have some clips in music magazines like Fader and Pitchfork. So it's definitely a topic I'm really passionate about. I love just talking about it.

1:27Sheena Butler-Young: Awesome. So let's start with ASAP. Your story sort of frames ASAP as the case study for this, the case study of hip-hop meets fashion and then an icon emerges. Why was he a good choice? What was so special about ASAP?

1:40Brian Baskin: Yeah, I think what makes ASAP Rocky so special is that he's like this generational talent who's just redefined, I guess, artists' relationship between hip-hop and fashion, right? Like, hip-hop is this genre that's always had these style icons every decade, you know, whether it's Rakeem or Big Daddy Kane or, you know, someone like Kanye West in the 2000s and 2010s. But I think what made ASAP Rocky said it different was he came out the gate as this rapper who really declared that he was into high fashion, you know, on his breakout single, Teyso, he said that he was into Rick Owens and Raph Simmons.

2:15Brian Baskin: as a teenager growing up in New York City in the early 2010s listening to this music that was actually how I got introduced to some of those brands you know I never considered any of those designers before I was mostly into like sneakers and streetwear brands like Supreme which has these really organic connections to that genre of music but it wasn't like I guess high fashion or runway fashion right and he's been committed to that since he came on and I think that's what makes him such an attractive talent for just like all these brands today is that he has this real organic love for just runway fashion, high fashion, and also just like, you know, streetwear and like street style.

2:52Takanashi: So he was doing this not because the brands were paying him, at least initially, but just because he liked the brands, right?

2:58Brian Baskin: Yeah, yeah. It was this like real organic love. I mean, when he first came on to the C &H one in like the early 2010s, he built this whole fashionist around these like goth-esque like fashion brands such as like Y Free, Hood by Air, you know, bygone streetwear labels like Black Scale. And, you know, by the time it released his debut album, he had this song called Fashion Killer that really just, he sort of just, he really used this track to just claim that he himself was like the best dressed rapper to emerge from where we now refer to as the blog era of the early 2010s.

3:28Sheena Butler-Young: I love that Fashion Killer video. Rihanna was in there, who's now the mother of his three children and their partners. How would you otherwise, so let's assume that some of our listeners have not seen A$AP Rocky. I don't know how that's possible, but like, how would you characterize this aesthetic? Because you hinted at this earlier, it sort of ran counter to what the hip hop aesthetic was presumed to be at that time. Like he had something different. What is his look?

3:53Brian Baskin: It's so tough to say because A$AP Rocky to me is just A$AP Rocky. But when I consider just like the history of like hip hop fashion icons, I always draw comparisons between him and Cameron. And I know this news here probably aren't aware who Cameron is, but I say that because, you know, they're both from Harlem. But it feels like there's a regional undertone that runs for how you set Rocky dresses. That feels like it's very true to New York fashion, New York style, New York street style, basically the same way how like, you know, Run DMC came out in the 80s. their whole look was basically inspired by New York City B-boys that, you know, how they dressed in tracksuits and, you know, laceless Adidas superstars.

4:30Brian Baskin: Like, A$AP Rocky sort of challenged that same energy. I think that's what really distinguished him from someone like Pharrell or Kanye West. Like, yes, A$AP Rocky loved fashion and he loved designer brands. And that's always been, like, consistent with the best-dressed rappers. But I think what kind of set him apart from everyone else is that, you know, even to this day, he still wears clothes that remind you exactly where he's from you know he'll come out wearing beef and broccoli timberlands you know um a really great example of this like hybrid style he's sort of built or distinguished himself with is that at the met gala last year he arrived wearing this super dapper suit but he layered it with like a very big coat that had these like vocal straps on the cuffs anyone who grew up in new york in like late 2000s and early 2010s know that's a reference to this jacket called a marmot biggie and there's a super long story behind that coat that i can't get into if i encourage anyone who's interested to read an article that I wrote about it for like Complex like five years ago.

5:23Brian Baskin: But it's like how North Faces got popular in the 90s. It's just a jacket that was embraced by youth of color in New York City, kids in uptown New York, the Bronx, you know. And Rocky makes these like authentic callbacks to just these regional New York style trends. And I think that's what really distinguishes them in this space, you know.

5:38Takanashi: But today it's more a mix of what he's wearing personally and then all these deals he signed. I mean, it may have started out organic, but now, you know, he's designing Ray-Ban sunglasses glasses and Montclair puffer coats and Puma sneakers. And he released a capsule with Quince. I mean, I'm guessing Quince was not like an organic expression of his love of fashion. No, nothing against Quince, but it feels different than what we've been talking about. And I'm curious, I mean, has he maintained the authenticity and the general vision that you're talking about as he's also embraced the commerce side of it?

6:13Brian Baskin: I think he tries his best to. Sometimes when I look at partnerships like what he did with quince um i do question like if it's really you know authentic collaboration but i guess at the end of the day it's like a white t-shirt which is like also a staple to like just hip-hop style probably so i think he always finds ways to kind of like give it the twist that he's known for and just try to tie it back to something that feels authentic like you know he did a collaboration at cash app where on paper it kind of sounds ridiculous right like why would you collaborate with like a payment services thing but he ended up using has the opportunity also just like release apparel from his own designer collection AWGE so i think he tries his best to kind of make it seem authentic at the very least i mean i think one great example that came out there like yesterday was he did this ad for raybon that like basically referenced the 90s hip-hop movie belly he got nas in this campaign they recreated a scene with him and

7:07Sheena Butler-Young: his character sincere from the movie man i get a phone call from flaco this evening he want to meet in Harlem. Funny thing is, it's the same restaurant where I last met with his pops before he passed.

7:17Brian Baskin: And like the glasses are actually inspired by the same ones he wore in this like 90s film that's become a very iconic reference point for a lot of designers or a lot of brands when he wanted just a reference 90s hip hop culture. So even though the references kind of played out at this point, I still respected that he did build something that felt like authentic and real to the culture.

7:36Sheena Butler-Young: So basically, A$AP Rocky is amazing, right? He's a star. We've just listed like the full gamut of brands that he's been able to collaborate with. But I think what we're getting at next is that what tends to happen in fashion, but also elsewhere is that someone becomes a go to brands start to get lazy, you become the easy pick for every collaboration that a brand is coming out with. Do you see that happening with an A$AP Rocky? I think that's the point of your article is that brands can start to over rely on these iconic figures like an A$AP Rocky, like a Pharrell, like a Travis Scott, some would say.

8:11Sheena Butler-Young: Do you see that starting to happen? And is there a pipeline building up?

8:15Takanashi: And before you answer, I also want to add that this goes way beyond hip hop. I mean, one of my favorite headlines we ever ran was Dua Lipa Again. That was just the headline. I love that. You can definitely read it in that Dua Lipa Again. I think that fashion has a tendency to glom on to certain familiar names that they know everyone's heard of and is interested in. But yeah, talk about specifically in the world of hip hop, how this has played out.

8:42Brian Baskin: Yeah, I think you're absolutely right. We've definitely relied on certain artists and sort of crushed onto them, like, you know, A$AP Rocky, Pharrell, Travis Scott, you know. And I think it's like we have a tendency to do that just because it's like, you know, these artists, they have just like such long resumes where a marketer can just point to like several examples they've done in the past and they can already see the result of it. Right. So I think it's a lot harder just in general to just sort of take your chance on something new, something different. and I think of Asap Rocky specifically I think he's so attractive to just consistently work with because outside of the music he's just built this life that I think just engages just regular people like you know he's partners with Rihanna he has like three kids he's a family man and it's like it's really I think hard to like dislike someone who just seems so wholesome and just so charming outside of music as well a lot of his fan base are basically growing up with him right so all these consumers who were teenagers when they first started getting into the world are now adults who are probably experiencing the same things he's experiencing they're probably half kids now they probably have partners and I think they almost see I said Rocky is like this is like the coolest version of adulting or something like that so I think that's also why so many brands

9:53Sheena Butler-Young: turn to him so the other important thing I think we have to get into in your article Leigh does a really good job of threading the needle here there is a subtext there is a perception that maybe some fashion brands, especially the super high-end ones, don't want to do the legwork of reaching into the hip-hop community and making that association with these stars. So they easily reach for the safe bet, the one that their other peers have worked with, the one that is proven, not just because they can drive revenues, but because they feel safe and maybe they don't want to do that with other artists.

10:28Sheena Butler-Young: How has that come up in your research when you were reporting this

10:31Brian Baskin: story did you did you get into that yeah I mean I think that's almost like an issue with sort of like the how generally fashion is a business that like extracts culture but doesn't necessarily get back to it as much as we'd like for the industry too right like I think they put rappers in the front row and they they put they put artists in campaigns but I think you wonder if who's making these decisions behind all this. And it's usually not people who are necessarily truly invested in the culture as others maybe. And I think, first, I think those companies have to strive to just make their workplaces more diverse and bring more diverse perspectives who could probably argue that, okay, this name here is someone that is just as viable as all these other talents that we've used for years.

11:21Brian Baskin: And here's why, because they have a true just resonance within the culture.

11:26Takanashi: My question is, why is fashion struggling to find new artists? I mean, there's nothing wrong with A$AP Rocky, obviously very beloved and effective brand spokesman, organic, all in one. But I was looking at a list of lists put out in index in 2017 of the most influential rappers in fashion. I'm just going to read it. So one and two are Kanye West, Nicki Minaj. I think we can strike those off. But then it goes Pharrell, Cardi B, Drake, like ASAP Rocky, Kendrick Lamar, Travis Scott. That's almost 10 years ago. And it's basically the people we've been talking about this entire episode about fashion in 2026.

12:04Takanashi: So where's the next generation?

12:06Brian Baskin: It's so hard for us to like detach ourselves from these names because, yeah, it truly like when I was on the Maytown agencies, they all mentioned how like this process of sort of shaping or molding these like future celebrity ambassadors is very much a slow burn, right? Like you kind of have to one look out that there's like a real organic connection. These artists have the brand. So like, you know, Central Sea is like a much younger artist. He's very new. He's not necessarily like a household name yet. He just cracked the Billboard 200 like last year. Granted, I think his album placed in the top 10, which is, I think, one of the biggest debuts for a British rap star in like history, actually, which is pretty impressive in itself.

12:47Brian Baskin: but that's the thing it's like he's not someone i think who people are checking like asap rocky right because he's so young you know and so for i've never wanted to talk into someone at nike and nick schornberger who like kind of leads or kind of helped shape these partnerships he was telling me what they really look for first it's just an organic connection right that's how their partnership with drake started that's how their partnership with travis scott started there was this organic connection to the brand and like i guess a lot of sport as well so in central sea specifically, you know, if you go to his earliest videos, he's wearing a lot of Nike tech.

13:19Brian Baskin: He's wearing Nike Air Maxes. He like, he's very passionate about the brand's real, real connection to it. So I think you have to see that first. And from there, you have to just also just sort of, you know, go back and forth with it. You know, it might just, it might start just like, okay, like for a luxury brand, I start just dressing the artist for a red carpet appearance. Then it might go to like putting them in the front row of the show and then seeing maybe how people react to those moments.

13:43Takanashi: Is there a danger though that fashion has just become too risk averse? I mean, it just seems looking at who the top artists were 10 years ago and today that sure they can dress, you know, an up and coming rapper for an award show, but every single major campaign, they're just going to default to Travis Scott or A$AP Rocky or one of these safe names. They're luxury fashion, I mean, this is one of the knocks against it, is incredibly averse to change. And there's a danger in that, right, Leigh?

14:20Brian Baskin: Yeah, yeah. And I think the world just, I think, just moves a lot faster now, you know. And I think we got to consider how, like, there are a lot of these, like, you know, emerging artists who I think people would like to just pan as, like, a TikTok, like, you know, one hit wonders, you know. But at the same time, it's like, with how fast people forget things, remember things, like it's like why not just take that chance you know at the end of the day even just a social media post it doesn't have to be like a global campaign there are ways i think you could engage with emerging talent and it doesn't have to be like an insanely huge commitment you know and i think it would be nicer to see just like luxury brands kind of explore that because i feel like they're kind of want to engage with it but it's engaging from like a very far distance you

15:03Sheena Butler-Young: I was thinking about, you know, what Brian said around risk. There is a true cultural payoff that brands are missing when they don't take that risk. Right. I think there's the headline of Dua Lipa again is getting after the fact that like, is it moving the needle anymore when it's the same person? Like it's safe, but what does it actually do for your brand? Like what does a mass star like that actually do when they're used over and over again? Is anyone surprised to see A$AP Rocky on a red carpet in Gucci again?

15:32Takanashi: Or do you even associate even A$AP Rocky? I mean, do people associate the brand with A$AP Rocky or are they just releasing A$AP Rocky? I see ads all the time where it's such a flashy, well done, clever ad. And then I'm like, wait, that was an ad for mayonnaise. Like I, you know, like not that A$AP Rocky is doing a mayonnaise ad, although, you know, but you know what I mean? Like, I don't know how much it's doing for the brand when the ad is really for the star in the end at that point.

15:58Sheena Butler-Young: it becomes interchangeable right like you look at that and i don't know if this is ray-ban or marine sayer or if it's puma like i see him and he looks great but like am i really am i really taking note of the brand and building any affinity i think that's the real risk that brands may not be thinking about it's safe but is it actually moving the needle yeah yeah and also i think it's

16:18Brian Baskin: just like are you engaging like just a new younger customer audience right like you know i think i I admire how brands like Vans and Mew Mew have like, you know, I wouldn't say like this rapper name like Netspan's close to becoming like anyone. Asap Rocky, maybe. Yeah, like he's far from becoming a household name, but he has he's like over indexed on all of us like Gen Z listeners. So like to me, it catches my eye and makes sense when I see him on the Mew Mew runway or I see Gucci dressing. Same goes from just like Playboy Cardi being put on like a Supreme shirt. You know, it's like that's an artist who almost for 10 years now is, I think, really shaped street style, street fashion and just shaped how an entire generation of hip hop listeners dress.

17:04Brian Baskin: Right. I mean, there's a whole TikTok trend that's dubbed Opium Core that's basically based on how he dresses and how people within his own like artist roster dress. Yet it shocks me that one, the only brands that like collaborate with him are not like they're not major brands necessarily. Like the biggest one I could think of is like Peli Peli, you know, it's like, which is like a, which is, which makes sense. Cause it's like Peli Peli is like a hip, it's a, it's a leather jacket brand. It's very, it's had been invested in hip hop for like over 50 years. So of course they're, they're looking at talent like him.

17:37And I don't know.

17:38Brian Baskin: It's just like, it is bizarre to me sometimes.

17:40Sheena Butler-Young: Maybe that's the point, right? Like maybe like, because then with Westside Gun or Action Bronson, some of the people that you mentioned that are up and coming, when they make the leap whatever it requires them to make the leap from that to the next big star then we'll be talking about them on the debrief about how they're the new low-hanging fruit like

17:56Takanashi: is that the point yeah talk about action bronson and new balance because i i think it's their new balance is a huge brand but like when they went to a hip-hop artist they did not go to asap rocky

18:06Brian Baskin: they went to action bronson yeah i think there's a lot of strength and just kind of collaborating with artists that aren't necessarily like charting super high in a bobo chart but they have these really passionate niche fan bases you know action bronson is definitely someone who's like he's not like a kanye west you know he's not like a pharrell he's not he's nowhere near that like and honestly as if he's not necessarily like a fashion icon even in that sense but he's a personality and he used to have his own tv show and all this stuff and like he just built this niche fan base that really really loves what he does and i think they love his like kind of quirkiness and his style and then you have someone like um west side gun collaborating with sakini recently and i think that's also interesting because it taps into the server you know it's like he is perhaps like the biggest hip-hop surf in a niche of hip-hop which is like east coast boom bap revival i think another good example i could bring up that's outside of secret space it's like you know polo ralph lauren they recently like re-released this jacket called the japanerak and this is like a jacket that is super coveted by people that collect polo it's like a jacket that it resells for like 80 like 1500 to like 2000 dollars on on the second hand market right it came out in like i think the late 2000s i believe and how that jacket got popular was such an intriguing story because it was actually an item that went on clearance at the time like people didn't want this coat but what happened was like there was this rap duo from queens named timeless truth and this is a rap duo who they don't they're not again they're these are not like mainstream names at all right but they're polo collectors who had this outsized influence on a larger polo collecting community a larger polo collecting culture and when they wore this jacket one of their most popular music videos which really had less to this day it has less than a thousand likes on youtube less than 40 000 views they turned this jacket that went on clearance into like a modern day polo Ralph Lauren grill so when this jacket came out for a collaboration of the Japanese label beams like two weeks ago it sold out in seconds and it's the resale value has maintained you know it's it's like people are literally flipping these jackets right now for like 1500 to 2000 dollars like as we speak and it's just like I think that just goes to show the power of working with like artists who just aren't necessarily the flashiest names in the world you know it's like and I mean to clarify this collaboration wasn't a collaboration with the artists but these artists made the jacket what it was that's fascinating so it sounds like we've

20:40Sheena Butler-Young: ended on the fact that maybe fashion doesn't need to try to find hip-hop's next biggest or maybe there's two lanes here and also by the way Leigh and I talked about this a lot offline as you were working on the story it's not that fashion needs to ordain someone in hip-hop as cool or fashionable anyway. But it sounds like you've described two distinct, but maybe equally potentially successful lanes that artists go down in terms of their fashion collaboration.

21:05Takanashi: I think that is so well put, Sheena, and also a great note to end on. So, Leigh, thank you so much for joining us today.

21:12Brian Baskin: Yeah, thank you, Brian. Thank you, Sheena. Honestly, like, I feel like I could talk all day about this and I really appreciate you asking me questions about it.

21:19Sheena Butler-Young: Please be sure to check out Leigh's article, How Fashion Picks Its Hip Hop Style Icons, at businessoffashion.com. This and other stories are available to BOF professional subscribers only, and you can find the links in the episode notes. You've been listening to The Debrief, produced and edited by Olivia Davies and Eric Bria. I'm Sheena Butler-Young.

21:37Takanashi: And I'm Brian Baskin. We'll be back next week with a new episode. Thanks so much for joining us and be sure to follow us wherever you get your podcasts.

22:09We'll see you next time.

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