A Little Bit Cooler: The Lasting Impact of The Cool Kids on Street Fashion

The Cool Kids. Not the lukewarm kids, not the hot kids, not the tepid kids, not the warm kids. The Cool Kids. As so eloquently stated by Hanibal Burress at the beginning of their most recent project, 2017’s Special Edition Grandmaster Deluxe, the Cool Kids are very much what their name entails. The two-man group has quietly been setting trends, influencing styles, and driving street culture since they burst off the Internet and onto the scene with “The Bake Sale” EP  in 2008, and to this day have never fully received the credit they deserve for being the tastemakers that they are, both in music and fashion.

Meeting through a chance encounter on MySpace in 2005, Detroit’s Chuck Inglish and Chicago’s Mikey Rocks (now known as Sir Michael Rocks) brought a unique DIY aesthetic to the table since the day their debut album was released. Kanye West showed us in the mid-00’s that you didn’t need to make gangster rap to be cool, and Chuck & Mikey expanded on that by showing us that you can do it with your friends on MySpace and YouTube, becoming the OG internet rap influencers (sorry Odd Future) in the process.

But The Cool Kids were much more than just quirky, underground rappers. On the fashion front, they spoke to the streets with their style and flair like few artists before. They’re the rare fashion icons that you — with a little bit of hustle and innovation — can afford to dress like. They and their style were and still are accessible, relatable, and … well … cool.

When they burst onto the scene, The Cool Kids made dressing “hip-hop” feel real again. Ever since its humble beginnings, hip-hop style has always been about making it work with what you have, no matter if you’ve got $20 or $2,000 to spend. That independent spirit got lost in the excess of the early 00’s, when “style” was all about who had the most ice on their neck or the biggest rims on their Hummer. In a period of extreme maximalism (not unlike what we saw starting in 2017), Chuck Inglish and Mikey Rocks brought hip-hop’s DIY aesthetic and independent spirit back to its fashion.

If you’re truly stylish, you should be able to stunt on anyone in a thrift store outfit.

In our current hype-driven society where you can get lost in the sauce more rapidly than ever, spending money you don’t have to impress people who don’t care about you, the lessons The Cool Kids taught us about being yourself and wearing what you like a decade ago are more necessary than ever. They let us know that style is more about how you wear your clothes than the clothes themselves. In today’s homage, we’re exploring the main facets of the duo’s style and shining a light on how ahead of the curve they really were.

Don’t believe any of the aforementioned facts? Think we’re just talking shit? Hard examples here.


Everything 90’s is currently enjoying a lion’s share of the street culture spotlight. Classic pieces from Polo, Tommy Hilfiger, Nautica and more are highly sought-after and can reach outrageous prices on the secondary market. Many brands release “heritage” collections (modern remakes of their popular-again vintage pieces), and a style that was once obscure has now become mainstream.

However, when The Cool Kids came of age in the mid to late-00’s, hip-hop was embracing a period of extreme maximalism with artists like 50 Cent and Kanye West in a contest to see who could wear the most chains and buy the most luxury goods. It was uncommon, even strange, to see a rap artist in vintage pieces. The Cool Kids were the first to bring a thrifted, DIY look into the spotlight. There was nothing quite like it.

Their retro style, full of old-school jackets, vintage snapbacks — well before TI$A, Tyga and Chris Brown championed the movement and Driicky Graham’s awful “Snapbacks and Tattoos” was an unfortunate hit — and colorful, hard-to-find kicks struck a chord with many a fashion-forward individual. You didn’t have to have the deepest pockets or the most connections to dress like the Cool Kids. You just had to know where to look to find great vintage pieces.


High-low: a style that entails mixing one or two luxury pieces/accessories with regular goods. It can be a challenging look to pull off, as there’s a delicate balance that needs to be struck between expensive and inexpensive. When done incorrectly it screams “try hard,” but Chuck and Mikey were going high-low before it was even a term in fashion’s lexicon. They weren’t trying to make a fashion statement. They were just being themselves, and their modern fashion sense mixed with a classic 90’s flair suited their music (itself a mix of old and new) perfectly.

By mixing high-end accessories like Cartier glasses and the occasional gold chain with accessible pieces like Nike SB’s and vintage windbreakers, The Cool Kids acknowledged the status afforded to them as successful artists while not turning their backs on their unique style. Not everyone can afford an outfit composed entirely of designer goods, but most money-conscious, fashion-forwards individuals can afford to squeeze a designer piece or two into their wardrobe.

The Cool Kids were able to do this with no effort. High-low is a look that was originally born out of necessity, and they pulled it off so smoothly that it went almost unnoticed by the general populace. However, as everything that’s “cool” eventually does … it caught on. Nowadays, going high-low is one of streetwear’s most popular fashion statements. Chalk up another first for the duo.


Your style consists of more than just the clothes you wear: it’s also how you carry yourself, how you speak, and what your interests are. Everyone loves buying clothes and kicks, but not everyone loves the history and stories behind the product. A facet of Chuck and Mikey’s aesthetic that made them extremely relatable? They’re sneaker and gear nerds, just like a vast majority of their audience is. And they love bikes, even devoting a song to their custom Dynos and shouting out BMX legend Nigel Silvester on The Bake Sale.

In a recent interview with Hypebeast Radio, The Cool Kids spoke on their experiences skipping school to buy Jordans, browsing Hypebeast to learn more about the culture, and being early adapters of social media. At the dawn of the “rap internet”, they were hip-hop’s everyman group, extremely skilled producers and lyricists who were still down-to-earth and loved the same things as most of their fanbase.

It’s easy to be inspired by someone that you feel you can relate to, and The Cool Kids have always offered an aesthetic that’s relatable — yet still just aspirational enough — all at once, inspiring kids the world over to dress and act differently.


A rapper can’t be a true fashion icon without a few hard bars about their fits and their style, and The Cool Kids have more sartorial bars than almost anyone in hip-hop, now or ever. Here’s a few particularly legendary style and sneaker rhymes from their expansive selection.

You still on Ian Connor page trying to pick what to wear, yeah//These peasants fresh as me? Tell me how//They still distressing tees on they couch//Rock band tees and bands they don’t know nothin bout// You heard of Iron Maiden once? Bro, that don’t even count.

Aww, you judging me dog? Please, you shop at the mall//Me? I shop at boutiques, limited quantity sneaks// Where do these quantities be? Maybe they all on my feet. 

It’s hard to believe but swallow it//So much game I that I could put it in a bottle and sell it to lames//And getting graphics in ya fade was fresh in the day//But it was jacked by the losers, I’m bout to say screw it and//Grow a jheri curl, wear a diaper like Cupid, or something else stupid and see if people do it// and if they do it then that proves it//people are just losers and they’ll anything if someone cool do it//But they won’t do it first so I guess they not cool//And it’s the end of the verse so I’m chucking that deuce.

Friday night nice, Saturday sharp//Edge upon the hairline, side tapered and ball//Sunday winning in the linen shorts sent from the mall//Pieces out the dry cleaning, stitched seams and all//That glitters ain’t gold but this is//Cars hoppin’ in em//Mars spike editions at the Palace like the Pistons.

Jump off the porch to a Porsche//Tryna stay away from the courts//Air Max on my Force, Bo Jack not the horse//And the trap got the works, take it back to the stores//Off the same plate but we don’t share forks//My n***a this the gospel so we don’t mince words// We wild out, birds fly south a long route// How loud is the bag? If it’s Gucci, what’s the tag? 

Now from the Starter to the Nautica, the Cartier//See I’m the n***a you was lookin’ to to start a wave//Don’t make me finesse and hop into the back of that Maurice//That Banco Piece edition in the back of all my car seats//Tornado flavor, flip Motorola Razr//I been callin’ plays since Gold And A Pager.


And that’s a wrap. You’re done with that big chunk of reading. Thanks for sticking with us. A story the nature of Chuck and Mikey’s cannot be told in just a few words, and now you just need to take away some lessons. You can learn something about style, flair, and individuality from The Cool Kids, no matter if you were around when their first project dropped or if this article was your introduction to the legendary duo, so take what you can from their style, mindset, and aesthetic. See? You’re a little bit cooler already.


Were you into street culture when The Cool Kids hit the scene, or was this piece your introduction to them and their legacy? How have they influenced your personal style? What’s your favorite Cool Kids track or album? Sound off in the comments or let us know on Twitter!


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