Scene from Fresh Dressed
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After flipping through the September fall fashion issues of my favorite magazines with black “it” girls such as Beyoncé, Kerry Washington, Serena and Misty Copeland on their covers, I’m unusually interested in clothes. All that paging through magazines got me wondering: Where are all the black-owned fashion brands? Yes, of course well-known black brands still exist. Tracy Reese and Byron Lars are two of my favorites. 

Digging into the rabbit hole of black designers led me to Fresh Dressed, a fascinating documentary about the foundations of urban fashion that features some of the biggest names in fashion (Dapper Dan, Andre Leon Talley) and hip-hop (Kanye West, Nas). And it conveniently airs on Vimeo on Demand. (The film will also air at 9 and 10:45 p.m. EDT Thursday on CNN.) One late-night click on my PayPal account and I was immersed in the world of pregentrified New York and hip-hop’s early years, which started the urban fashion-apparel market. Sweet! 

Ready to take a walk down memory lane or learn the secret to how the brands so many of us wore in the ’90s became hot (then not)? Check out Fresh Dressed. Here are 10 reasons the doc is worthwhile:

1. Unique fashion inspirations.

Customized leather jackets underneath denim vests—a fashion staple that was worn by street-gang members who wanted to identify their affiliation—were inspired by 1969’s Easy Rider, a film about two bikers.  

2. Jamel Shabazz photographs.

Brooklyn, N.Y.-born Shabazz spent the ’80s taking iconic pictures of black street style and capturing the culture. His driving force? “[Black style] is interpreted around the world as just being fly,” Shabazz says in the documentary. “What I see is pride and dignity. I wanted the world to see [us] as something unlike they had seen before. That despite people’s condition, they were able to maintain a great deal of integrity, and it is shown in the way people dress and the pride they take in having clean sneakers on.”

3. Random hip-hop fun facts. 

Before Play of the rap duo Kid ’n Play was a rapper, he was a graffiti artist who used denim jackets as his canvas. “People would pay me to paint their names on their jeans,” says Christopher “Play” Reid. 

4. Dapper Dan was more popular than Louis Vuitton (among black people).

The (in)famous Harlem designer and boutique owner was best-known for merging hip-hop fashion sensibilities with the logos of European fashion houses, such as Louis Vuitton and Gucci. Think tricking out the upholstery of Big Daddy Kane’s car with a red-and-black Gucci monogram print or maybe a red leather Gucci sweatsuit for Bobby Brown. “I blacken-ized [luxury] fashion,” Dan boasts in Fresh Dressed. “I made it so it would look good on us.” 

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Nas, a producer of the documentary, takes the boasting a step further: “Dapper Dan was Tom Ford before Tom Ford,” says the rapper. “He had the foresight to do what they [luxury brands] started doing five years, 10 years after him.” 

5. The genesis of fat laces in sneakers.

Before wide laces were sold ready-made in stores, sneaker aficionados had to create their own by taking the laces out of the shoe, stretching them, starching them and then ironing them.

6. Mayor’s closet. 

I’m not so into sneakers, but even I gasped looking at the walk-in closet of sneaker aficionado Mayor, who boasts of going 7.5 years without wearing the same pair of shoes twice. (That’s 2,737 pairs.) He keeps his collection, which includes a significant number of Jordans, in a row of plastic containers that are as tall he is and estimates that his collection is worth more than half a million dollars. 

7. Rediscovering the Lo-Lifes. 

This was a well-known “gang” in Brooklyn that didn’t identify itself by colors but by fashion logos, one in particular: Polo. Its criminal activity was mainly shoplifting Ralph Lauren clothing from department stores, and status in the group was determined by who wore the most exclusive wares best. For some, such as Lo-Life leader Thirstin Howl the 3rd (yes, like the millionaire from Gilligan’s Island), fashion is really that serious. 

8. Learning how Tommy Hilfiger became so popular among black people. 

Instead of offering endorsement deals to famous rappers, Hilfiger offered free clothes to the MCs—and in the neighborhoods where they came from. “Tommy Hilfiger would show up in the ’hood and open up a trunk with clothes,” recalls Ralph McDaniels, who hosted the popular hip-hop TV show Video Music Box. “It was the drug dealer giving you a free hit. It was smart. He knew exactly what he was doing.”

9. That time GAP unwittingly spent $30 million on a FUBU commercial.

LL Cool J signed on to do a Gap commercial but didn’t really believe that the brand respected hip-hop culture, according to FUBU executive Daymond John. The rapper insisted on wearing a FUBU baseball cap in the commercial and even dropped a line that included FUBUs tagline, “For Us by Us.” “It basically became a FUBU commercial,” adds John. FUBU eventually became a $350 million business. 

10. Learning that Tupac didn’t charge black people. 

At the height of his fame, Tupac Shakur took a meeting with Karl Kani in which Kani pitched him to star in an upcoming ad campaign. “I ain’t gonna charge you; you black,” Pac told Kani. “I don’t charge my people for nothing.” Two weeks later, they did a photoshoot … free. Kani credits Pac with introducing him to a global market. 

Demetria Lucas D’Oyley is a contributing editor at The Root, a life coach and the author of Don’t Waste Your Pretty: The Go-to Guide for Making Smarter Decisions in Life & Love as well as A Belle in Brooklyn: The Go-to Girl for Advice on Living Your Best Single Life. Follow her on Twitter.