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

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

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

Facebook Twitter Pinterest Run DMC in their signature hats and gold chains. Photograph: Sunshine/REX Shutterstock

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

Jenkins points out that in the early hip-hop scene, clothes were a way to transcend the poverty that surrounded most of those involved. Damon Dash, who set up Rocawear with Jay Z, talks in the film about how “if you go home and you got roaches and 10 people living in an apartment, the only way you can … feel some kind of status is [with] what you have on your body.” This may link back to the origins of “fresh” – the hip-hop look is about being pristine, never grimy. “That’s a major difference between hip-hop and rock’n’roll,” says Jenkins. “You’ll never find photos of hip-hop stars wearing thrift clothing.”

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

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

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

While there have always been connections with designer brands in hip-hop – see the Ralph Lauren-obsessed subculture Lo Lifes – these labels symbolise a kind of gold standard of European luxury. “With Kanye West it’s like: ‘I have something that you never will have,’” says Nielson. “There’s a form of self-aggrandising, to become larger than life because you can afford stuff in the upper echelons.” The need to have the latest symbols of status has its dark side away from West’s gilded world. Several people in Fresh Dressed mention the threat of sneakers being stolen from their feet, and there’s the story of a 2013 shooting in New York’s Bryant Park after a fight over a teenager’s Marmot coat.

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

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

Five staples of the hip-hop look

Cazal 607s

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

Facebook Twitter Pinterest Cazal 607s glasses. Photograph: PR

Cross Colours Originals T-shirt

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

Facebook Twitter Pinterest Cross Colours Originals T-shirt. Photograph: PR

Polo Bear sweater

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

Facebook Twitter Pinterest Polo Bear sweater. Photograph: PR

Marmot Mammoth

Sometimes called “the Biggie” because Biggie Smalls wore the coat, these now-discontinued parkas (which sold for up to $700) were so highly prized that one wearer was shot for his in 2013.

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

Yeezy Boosts

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

Facebook Twitter Pinterest Yeezy Boost Adidas Originals. Photograph: Adidas

Fresh Dressed is out in cinemas on Friday, and is available on DVD and to download on 9 November