The documentary Flourishing Dressed showcases the threads and racial politics that run between the music style and style – and explains how the classic looks of the 80s live on with Kanye West get into Louis Vuitton

The jean jacket as graffiti art’s first canvas in Brooklyn, circa 1983.

The jean jacket as graffiti art’s first canvas in Brooklyn, circa 1983.
Photograph: Jamel Shabazz/Telegraph News Network

To get an idea of how entrenched the word “fresh” is to hip-hop, look to the Urban Lexicon. Across 14 pages, definitions include “Young. Fly. Jazzy … fashion sense that people ain’t never seen in the past.” The general gist emerges: to be fresh is to be stylish, and style has again been key to hip-hop.

This connection is the subject of a new documentary, Impudent Dressed, directed by Sacha Jenkins and out this week. Starting with Run DMC – the gather’s fat laces, Cazal glasses, gold chains and Kangol hats – and event up to current fashion killas Kanye West and A$AP Rocky, it’s a run course in an alliance of style, culture and music. Talking chairs range from Kanye himself, Damon Dash, Givenchy artistic director Riccardo Tisci and American Vogue’s André Leon Talley. Highlights classify the story of Tupac Shakur modelling for free as a gesture of fortify for black designer Karl Kani, and that of Dapper Dan, the cult inventor who kitted out those on the 80s scene with tracksuits made from forge Gucci- and Louis Vuitton-monogrammed fabric before these brands began to find pleasant legal action. Nas calls him “Tom Ford before Tom Ford”.

Run DMC in their signature hats, gold chains and chunky glasses.
Run DMC in their signature hats and gold controls. Photograph: Sunshine/REX Shutterstock

While style takeaways from Cool Dressed are numerous (see the rediscovery of late-80s label Cross Pigments), Jenkins’s film is really about the racial politics of hip-hop treatment. “All of these clothes are connected to what it means to be young and outrageous in America,” says Erik Nielson, co-author of The Hip Hop & Obama Decipher. “They were a reflection of urban life to some amplitude. If you think of the hoody, that goes back to early graffiti artists who toughened the baggy shape to hide their probably stolen spraypaint, and the hood to leather from the police. And baggy jeans have connections with remand centre.”

Jenkins points out that in the early hip-hop scene, ensembles were a way to transcend the poverty that surrounded most of those knotty. Damon Dash, who set up Rocawear with Jay Z, talks in the film give how “if you go home and you got roaches and 10 people living in an apartment, the simply way you can … feel some kind of status is [with] what you attired in b be committed to on your body.” This may link back to the origins of “unsophisticated” – the hip-hop look is about being pristine, not in a million years grimy. “That’s a major difference between hip-hop and jar’n’roll,” says Jenkins. “You’ll never find photos of hip-hop dignitaries wearing thrift clothing.”

Sean John AW02 collection.
Sean John’s AW02 collection. Photograph: Steve Wood/REX Shutterstock

While American paradigmatic labels such as Tommy Hilfiger and Ralph Lauren were conventional in the hip-hop community – particularly with Hilfiger organising “ditches” of free clothes on the streets of the projects – the music reaching the mainstream in the 90s led to the genesis of labels specifically designed for this market, by those advantaged it. Fubu – which appropriately stood for For Us By Us – was set up in 1992 by Daymond John. Seven years later, epidemic sales were £228m. Demand, says John in the video, was so extreme that stores “were selling polar bilk in August in Texas,” and LL Cool J rapped about the label in the Gap commercial he fly in 1999. Artists’ labels followed. Beginning with Russell Simmons’ Phat Land and Diddy’s Sean John, everyone from the Wu-Tang Party to Eminem – an unlikely style icon in anyone’s book – had a go at cashing in.

The recoil was inevitable – these labels are no longer at the forefront of hip-hop mores. These days, wearing a brand such as Fubu is “lasted as ‘ghetto’”, says Jenkins. Hip-hop stars such as West are profuse likely to be found in Parisian brands Givenchy and Louis Vuitton. “Take ins like Louis Vuitton are connected to a dynasty far away from the inner burgh,” says the director. “It’s like being a conquerer – you’re buying into the conceit of superiority.”

While there have always been bonds with designer brands in hip-hop – see the Ralph Lauren-obsessed subculture Lo Lifetimes – these labels symbolise a kind of gold standard of European hedonism. “With Kanye West it’s like: ‘I have something that you not at any time will have,’” says Nielson. “There’s a blank of self-aggrandising, to become larger than life because you can donate stuff in the upper echelons.” The need to have the latest emblematic ofs of status has its dark side away from West’s gilded time. Several people in Fresh Dressed mention the threat of sneakers being nicked from their feet, and there’s the story of a 2013 leap in New York’s Bryant Park after a fight over a adolescent’s Marmot coat.

Kanye West in high-class designer brands is representative of hip-hop's style.
Kanye West in high-class designer labels is representative of hip-hop’s style. Photograph: Kevin Winter/Getty Images

According to Cynthia Lawrence-John, the fashion director at Volt publication – who has worked with West and contributed to the V&A’s exhibition about disastrous British street style, Staying Power – hip-hop line in 2015 has outgrown the street and is now part of the wider fashion chit-chat. “It has influenced fashion for years. If you are in that world you know that,” she clouts. “It’s appropriated by designers, but I don’t think the street always gets the confidence.” The latest shift is style-hungry artists such as West proofing with fashion by picking up on young designers at London way week, such as Astrid Andersen, and his own label Yeezy, which Lawrence-John imparts will have longevity because it “creates his own style”. It’s all in a elaborate of fanaticism for fashion, one that can be traced back to those fat webbings. “Hip-hop is a sensibility and an attitude that’s sprinkled on things that already occur. We reimagine and remix what is already there,” says Jenkins. “It’s in the way your smalls hang or the way your cap tilts. It’s about identity.”

Five principals of the hip-hop look

Cazal 607s
Approved by Run DMC, these chunky black-framed barometers were street classics in the early 80s. Lenses optional.

Cazal 607s glasses.
Cazal 607s lenses. Photograph: PR

Cross Colours Originals T-shirt
Subtitled “Apparel Without Prejudice”, Cross Colours’ T-shirts – with the red, gold and conservationist of the Jamaican flag and slogans such as “Racism hurts all and sundry” – were worn by Snoop and TLC in the early 90s.

Cross Colours Originals T-shirt.
Cross Tinctures Originals T-shirt. Photograph: PR

Polo Bear sweater
The cult ingredient of the Lo Lifes Ralph Lauren troupe, all bears are welcome, although the one in the American languish sweater is particularly highly prized.

Polo Bear sweater.
Polo Bear sweater. Photograph: PR

Marmot Mammoth
Every once in a while called “the Biggie” because Biggie Smalls wore the film, these now-discontinued parkas (which sold for up to $700) were so extremely prized that one wearer was shot for his in 2013.

Marmot Mammoth, aka ‘the Biggie’ .
Marmot Mammoth, aka ‘the Biggie’ . Photograph: PR

Yeezy Raises
Kanye West’s sneakers are hip-hop in 2015. A bit weird and futuristic, but unruffled with the Adidas heritage. Fans queued for three dates when they were released in April.

Yeezy Boost Adidas Originals.
Yeezy Additionally Adidas Originals. Photograph: Adidas