Watch the Tunes: Fresh Dressed

Historically, the four main elements of hip hop culture are MCing, DJing, Breakdancing, and Graffiti. Other aspects that are less prominent but nonetheless essential to the culture include fashion and entrepreneurism. The documentary Fresh Dressed, directed by Sacha Jenkins, the creative director of Mass Appeal magazine, examines the fascinating intersection of those dueling fifth Beatles of hip hop. Going all the way back to hip hop's roots in the leather-jacketed gang-culture of the Boogie Down Bronx, the film traces the history of stylistic trends through Cross Colours, Coogi Sweaters, the explosion of rapper-owned designer brands in the 90s, and beyond. For anyone who has fond memories of paging through the Wu-Wear catalog that was baked into the liner notes of Wu-Tang Forever, this is the documentary for you.

Next Wednesday Kanye will debut his Yeezy Season 5 line of wearables at New York’s Fashion Week. Whether you dig his clothes or think he should stick to rapping, Fresh Dressed argues that Ye’s desire to flex his muscles in the world of fashion isn’t nearly as innovative as he might wish it was. From its very inception, hip hop was all about aspiration. Founded on the backs of B-Boys and B-Girls dreaming of something better than the burned out buildings that abounded in New York’s late ‘70s bankruptcy badlands, style became inseparable from status. Status, or course, was reflected in the brands of clothing, which set the path for savvy designers hitching their wagons to rappers as a means of marketing directly to this new fashion conscious market. Young guns Karl Kani, Tommy Hilfiger, and Walker Wear, among others, leaned in and got rich by hopping on at the ground floor.

Not only was style a projection of hopes and dreams, it was a reflection of geographical identity. Back in the day, if you wanted to know which borough a kid was repping, all you had to do was see if his sneakers matched his track suit or what brand of jeans he wore. There’s something almost quaint in this hyper-awareness of the subtle differences in the ways you dressed would be a statement of place. It’s the sort of thing, like hip hop itself, that could only come from New York’s melting pot system of boroughs.

Hip hop has always been more than just a genre of music. By maintaining those multi-disciplinary pillars of expression, it’s been able to remain inclusive to everyone It’s because of those ancillary aspects of its culture overall that the medium continues to thrive to this day. By focusing on the roots and various evolutions in the world of hip hop fashion, and by extension various fashion lines related to rappers, Fresh Dressed gets into the deep nitty gritty of the culture. I mean, we get to see interviews with Dapper Dan, the Harlem tailor who spent the '80s remixing Louis Vuitton and Coco Chanel in the same way that Grandmaster Flash cut up records on the wheels of steel. What’s more hip hop than that?

It’s a bit of a bummer, I thought, to find out at the end of Fresh Dressed that hip hop fashion trends can’t seem to shake the sense of perpetual aspiration, and the insecurity that it belies. There are lots of reasons that most of the smaller boutique rapper-owned brands went bust. Chalk it up to a suddenly oversaturated market, lots of haphazardly rolled out product, or the bad business of kids getting shot up over their Jordans, but the real reason underneath it all according to Jenkins is that the relative old guard brands like Polo and Gucci are just too insurmountable as a identifiers of upward mobility. Sure FUBU might stand for For Us By Us, but apparently it still has a ways to go to break free of its relative flash in the pan status.

I brought up Kanye earlier not just because he’s all over this documentary, but also since, even if you think his shoes are trash, he’s undeniably one of the best chances hip hop has to break into fashion on fashion’s terms. No matter how hard he tries, though, he might never get past the “new money” stigma that has hamstrung literally everyone that’s come before him. No matter how successful the umpteenth Yeezy Season might be, I guess, at the end of the day Migos is still gonna be name dropping Versace on into the sunset and it just is what it is.

I don’t want to say that we’re running out of new ways to approach hip hop in documentaries, and music in general really, but I get the feeling that a just-the-facts direct approach is getting played out. We already explored some of the fringes of hip hop in this column with Stretch and Bobbito: Radio That Changed Lives, and Fresh Dressed is easily on that same level of greatness. You can literally see people from every era in rap history light up in interviews, energized to have the opportunity to talk about this much less well known aspect of the culture that they have lived and breathed for so long. The joy is infectious and makes for a wildly fun and informative film.