New York City fashion just hits differently. But unless you grew up in New York, you probably wouldn’t fully understand it. Sure, a lot of New York fashion trends like rocking 6-inch Timbs and Yankees fitteds have gone mainstream, but street style in New York City goes much deeper than that. The popularity of New York staples like North Face jackets and vintage Polo sweaters all come with rich cultural stories that have unfortunately been overlooked until recently. 

This is why a New York City-centric Instagram comedy page like @rayyyrayyy___ caught our attention this year. The 25-year-old college basketball player turned comedian from the South Bronx, who wants to be quoted as Rayyy Rayyy, has garnered over 100K followers on Instagram for his humorous videos that cover every aspect of New York City culture. Whether he’s sharing childhood memories of attending ill birthday parties at the long gone Mars 2112 in Times Square or war stories about New York’s “cane-era,” for New Yorkers, his videos are a trip down memory lane.

But some of Rayyy’s best videos focus on New York City fashion trends—particularly in the late 2000s and early 2010s. Back when rhinestone Pelle Pelles and Marmot Biggies were the most coveted coats, snakeskin Don C caps were a serious flex, and a Polo sweatsuit could hold you down for an entire winter. We hit up Rayyy Rayyy to hear his thoughts on the most iconic New York City fashion trends, the most stylish New York rappers, what an average New Yorker dresses like today, and more. 

How old are you and what neighborhood of New York are you from?
I'm 25. I'm from the South Bronx, Morris Avenue area. 

How and when did you start making Instagram videos?
I started about three years ago, around 2017 when I was in school. I was actually in school playing ball first, and then some good friends of mine, Travis and Sam, used to hang around me every day, and always told me: "Oh, bro, you funny. Like you could really be like one of those funny IG public figures.” But, I wasn't taking it seriously at first. I ain't really see what they might have seen at first. So, time went on, and then I really just had a serious talk with my friend Trav. He was just saying, "Yo, bro, you're naturally funny. You're not forcing it. You're just being yourself. You need to like to stick with it and roll it." After that, that's what I did.

Is Instagram comedy your full-time gig? Or do you have a job outside of that, too?
I don't really look at it as a job. I mean outside of that, I work at the DMV. But, besides that, with Corona going on and all that, I'm not really working right now. But with Instagram, I don't look at it as a job because it's something that I'm starting to enjoy doing. It's starting to become a part of my routine. I just look at it more as a hobby now. It's just something that eases my mind, and gets me away from whatever I'm going through. I use it as an escape route and a way to express myself.

There are a lot of popular New York City-themed Instagrams nowadays. You have like, New York Nico and Sidetalk NYC. What's the goal of your page, and who are you trying to reach with your videos? 
The goal of my page is honestly being myself, but also showing other people that you could be yourself. It's okay to be you, and just to throw your swag on it and make it something that everybody else can enjoy. I wouldn't even say I'm trying to reach anybody specifically. The crowd that I was trying to reach is just genuine love. I'm just trying to spread love. Do you know what I'm saying? If everybody wins, that's less violence, less hate, and more happiness and all that. So, I would just say that's really my goal, just to spread love and just to be yourself. You can just do whatever you want to do. You don't got to pretend or nothing.

Your videos touch upon everything from lame ass Select Bus cops to getting robbed for your T-Mobile Sidekick back in the day. Personally, your videos about New York City fashion have unlocked a lot of old middle school memories I've had. What was the best era of New York City fashion to you and why?
Oh, that's tough. I would have to say the Pelle era, around the early 2010s, right? That's when we had Marmots, the Biggies, the Pelles. Kids today wouldn't really relate. But the reason I would say, for me, that's the best era is because it was just so flashy. Everybody was standing out. It was like every day you had to put on a good fit, and with the Pelles, you were able to get creative with it. I mean you had different colors. You had the rhinestones. You had different designs and all that. And then, with the Marmots and everything with the Biggies, you also had different colors and different styles. It was also the True Religion-era, the Ed Hardy-era, and all that. That era was crazy because you even had people styling and going crazy with the B.B. Simon belts. 

What New York fashion trends do you think your home borough, the Bronx, created?
I wouldn't say we necessarily came up with the B.B. Simon wave, but the Bronx definitely enhanced the knowledge of the B.B. Simon wave, even with the song that was made, that came out of the Bronx. What else? I would say even with the way that we might have did it, the Bronx was just more loud when it came to the rhinestone Pelles and the B.B. Simon belts. 

How many Pelles and B.B. Simon belts have you owned in your own lifetime, you think?
In my own lifetime, you see, I never really ran through clothes because if you know, back then, it was hard to really come outside and keep your coat. People were going through it, but I just always managed to keep mine. I probably had like, maybe two B.B. Simon belts, and definitely two Pelles. I had a rhinestone and I had a regular purple Pelle.

Everyone talks about SoHo when it comes to fashion, but I want to talk about Fordham Road real quick. What do you think are or were some of the most important clothing stores on that strip right there?
If you are talking about back in the day, you had the Foot Lockers, the V.I.M.s, the Old Navys and all that. But, if you're talking about now, you got Acelo over there and Sneakerbox. You still got the Foot Locker and you got the Finish Line over there now. But, you got to stay out of the jewelry stores that be selling the sneakers. You can't go there. The only thing I can say is just be careful. You might have to take a shoe tester or something.

It's crazy now where you can buy Biggies on like Marmot.com or see Supreme dropping B.B. Simon belts.
That's another thing, too. I feel like New York has such a big influence on jackets like that. Even like the actual brands started taking it to them. When it comes to New York in the wintertime, jackets are a big thing. To certain people, it really matters what jacket you have. Right now,  the Monclers got the wave. Even a few years ago, you had the Canada Gooses, that was it. You had the Mackage jackets, some people call them Mac-age, but a lot of people don't even know you pronounce it as Mockage. But jackets are just a big thing in New York. 

I guess jackets like the Biggie made a comeback recently. Do you foresee any other New York fashion trends making a comeback again?
I could definitely see the Biggies or Merms making a comeback. I could definitely see Nike boots making a comeback. I could definitely see Nike ACG boots making a comeback. And I ain't going to lie. I'm going to definitely try to help make a comeback for Pelles. I feel like if I could pull that off, that would be dope. 

I don't know if you saw this, but I found it really crazy that you dropped this video of a beanie with a brim. What's crazy is that I saw Supreme drop the exact type of hat a month later. Do you think that's a coincidence?
That's crazy. I ain't know Supreme did that. If you tapped in with somebody from Supreme, you got to tell them to tap in with me. 

I ask that because Supreme is all about, I guess, making clothing that speaks to New York shit, right? So, they drop their own Biggies and Pelles. Do you fuck with Supreme?
Yeah, because all that means if they’re doing that, is that they're tapped in. They pay attention to what's really going on, and all that means is they’re giving the people what they want. You just got other brands that might just put out what they want us to like. All that shows is that you got people from Supreme that's really paying attention to either the streets of New York City, or even the youth, just to see what we still like. They cater to their supporters, so that's pretty dope.

Any clothing brands ever hit you up about the videos you've made? Because I think you've spotlighted a ton of brands in the past year or so.
No, not that I know of. They might have either just liked it, or anything like that. But, not that I know of. But, a lot of people are tuning in. That's been an understanding. Sometimes they might not tap in after the first video that they see. Sometimes people might be looking for other things, or they just want to see more. But at the end of the day, they either like it, or they share it. I can't ask for more, just that they show that they're paying attention. So I can't get mad at that.

What's your all-time favorite winter coat in general? Like, a jacket that you could have worn in 2010 that still feels valid today to you?
The Marmot Biggie. That's one of the best jackets, and you still got people that wear it today. I was even thinking about buying another one. 

What do you think about current New York City winter jacket trends today? Like, everyone wearing Monclers. 
I like it. I actually got two Monclers, just haven't worn the second one yet. I like the Monclers because they got different flavors, colors. It's flashy. It's New York type-ish. I even feel New York might have enhanced the Moncler wave, too. Once New York gets a hold of something, New York just always takes it to the next level, whatever we get a hold of.

I got another winter clothing question. What would you pick: the Polo sweatsuit or Nike Tech? Which one do you fuck with more?
Oh, that's tough. I ain't going to lie, I'd say the Nike Tech because I can say if the Nike Tech was out back then, I could see the Nike Tech wiping out the Polo sweatsuit. It just fits better and feels better.

I've learned a lot about some older New York fashion I've missed by just looking at your page, like the crocodile leather Mauri shoes or the Angela and Vanessa Simmons Pastry high top sneakers. Aside from Air Force 1s, what do you think are the greatest New York City sneakers of all time?
Oh, man. Besides the Ups? Either got to be the Foamposites or Jordans. I would say the Jordans, yeah. I can't specify which Jordan, but I would have to say Jordans. But, Foamposites was there... Oh man. You got me. I'm going to say Jordans. That's tough.

That Foam-era was crazy. I feel like I don't see too many heads wearing Foams anymore...
You don't. You will always see Jordans trending. I got on a pair of Jordans right now, so you will always see Jordans trending. 

Why do you think Foams kind of fell off, you think?
I don't know. I think it was just a time thing. As time go on, people get tired of things. I don't think it was nothing specific. It's just a different era, new styles, new waves. Some things continue, some things don't. 

What are some trends that you wish continued that got left behind?
I kind of wish the Pelles continued. I wish Polo sweatsuits were as big as they were back then, today. Another thing is B.B. Simon belts, even though you still see a lot of people wear them.  See, a lot of people don't understand. You got a lot of people that are running toward the designer. And back then, you ain't really run towards the Diors and the Pradas. I mean you did the Pradas, but now everybody is all Louis Vuitton and Dior this. People weren't Fendi-d or Dior-d out back then. You might have Gucci shoes or a Gucci belt here and there. 

You had this great video about G-Unit dropping the Reeboks and how crazy that took off in New York. And nowadays, you got kids going crazy over Travis Scott Jordans or Yeezy Adidas. What New York rapper would you personally want to see get a sneaker deal right now? 
I'm going to say Fivio Foreign. I feel like he would go crazy with a sneaker promotion, everything. But, I just see Fivio getting a little Nike deal, Jordan deal, something like that. 

Along with that question, who do you think is the freshest New York rapper right now when it comes to this fashion shit? 
Oh, wow. Freshest New York rapper when it comes to fashion. I feel like it's too much to choose from because you got people like Cardi B and Nicki Minaj. You have people like A Boogie, he know how to dress. God rest his soul, Pop Smoke knew how to dress. Lil Tjay. 

You know, a lot of people are sleeping on Jay Critch. Jay Critch knows how to dress, too. Jay Critch be having some drip. A lot of people be sleeping on Dave East, too. But, if I had to pick one, I would probably go with Fivio probably got it.

I definitely feel you when you say people sleeping on Jay Critch, for real. That dude got crazy fits.
Jay Critch got some shit, bro. Jay Critch knows how to dress. You can put Critch up there, too. Critch, he doesn't get enough credit for how he dresses. Son be putting his shit together.

Who do you think is the best dressed New York rapper of all time, you think?
It got to be the Dipset era. Because Cam knew how to put his shit together, Jim knew how to dress, but Juelz used to go crazy. But I'm going to go with Cam.

How did they inspire your own taste in fashion? 
They were loud with it. It was just the way they did it. It was just a New York thing, the way they swagged it. The way they did it. It was crazy. They always influenced you to take your own style and do your own thing. They had the blueprint.

A lot of your videos talk about how you had to be really on your Ps and Qs back then when rocking some of this gear. Not everyone could walk out of their crib with a $500 Don C cap and come home with it the next day.
That's a fact.

Do you think New York has chilled out in that regard, or no?
Definitely. I would definitely say New York has slowed down on that. But, back then, it was crazy. Met a lot of people going through hell coming out with nice jackets and all that. It was almost as if you had to travel with your friends everywhere.

Do you think some New York fashion trends like rocking fitteds, wearing Timbs or white Uptowns, have gone too mainstream? Or, are you happy that everyone is onto that type of shit now?
When it comes to Uptowns, you can never go too mainstream with that. I like that you see Atlanta rappers and people from Chicago, Ohio, and all over the world wearing Timbs. Just to know New York influenced fashion in that way, that's dope. That's big and gives a reason for New York to live on forever. 

When people make all these memes about New York, they always put those items on cartoon characters. If you had to dress up an average New Yorker today, what would they look like? 
An average New Yorker right now, he is going to have on some Amiris. You're going to put on some foreign sneakers, whether it's your Pradas, your Balenciagas, whatever. Right now, it's the Diors. The Diors got the wave, so you're going to do that. You're going to do the Amiris with the Dior. You're probably going to do a Dior sweater, a Louis belt with a pouch, and your jacket most likely, it’s going to be a Moncler. So you're probably going to have on the Moncler or the Mackage jacket. Some people are even going to have the Louis Vuitton jacket. I see a lot of people buying the Burberry jackets, too. Burberry's starting to make their way back in with the jackets. I don't really see a lot of New Yorkers wearing the fitteds like that, so that's going to be a typical fit. Amiris, foreign feets, Louis belt or Gucci belt with a pouch, and probably a Dior or foreign hoodie with a jacket. 

You already got this ill following on Instagram. What's the next step for you, you think? What do you want to see happen next?
The next step, honestly, I want to change the comedy game. I'm tired of just seeing the regular. For example, the music game, you got the industry, you a rapper, you will get on, you get signed, you make money, and you make a living off of it. That's what I'm about to do with this Instagram game. I want to actually go into making this into a way that people from New York or all over the world can make a living. There's a lot of opportunities on social media. So my goal is just to open the doors so that others could come in behind me and do something better, greater, or just eat and make a living. That's my goal. I just go with the flow. Obviously, I see a better following, more endorsements, hopefully TV. But, really what I did, I just go with the flow, and I just see me being better, smarter, and greater. In a better position than what I'm in now.

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