To coincide with Sotheby’s inaugural hip-hop auction, Highsnobiety teamed up with the auction house for a panel examining "The Rise of Hip-Hop." The conversation touched on appreciation, appropriation, the relationship between hip-hop and luxury, and the most pivotal moments in their tumultuous history.

One of the panelists was uniquely qualified to speak on the rise of hip-hop. At 76, New York couturier Dapper Dan has decades of experience straddling the worlds of luxury and hip-hop.

Below, we've selected some of his most interesting observations on how the two spheres have clashed and collaborated over the years.

On the pivotal moments in fashion

My mantra is always “follow the culture” and in fashion “be a translator of the culture,” give them the look that tells the story about who they are and what they’re saying.

When you look at the jackets that I did for Erik B and Rakim, you see the Five Percenter sign on one, but it’s a Gucci jacket. It’s royal, it’s gold and black, and that all Rakim, he’s Five Percenter. And when you look at Erik B. he represents Gucci. That would be one major pivotal point in fashion.

The next would be, when Jam Master Jay came to my store. He had a big, thick, gold adidas symbol on his chain that adidas gave to him. When he came out with that record, “My adidas,” that triggered a whole new era in hip-hop fashion because now the brands took notice.

The third is JAY-Z. Everybody and their brother and their mother’s brother were wearing jerseys. I went to a place one time [and] I’m the only one who has a suit on! People asking me where the bathroom was at. I’m from the underground and there were plenty of people making tons of money selling knock-off jerseys. JAY-Z came out with that rap thing, and he said, “You can’t be grown and sexy with no jersey on, you gotta have a button-up. You couldn’t sell a jersey for 15 cents. You couldn’t give a jersey away!”

Those were three pivotal points in fashion. And those are the points you gotta pay attention to.

On appropriation, appreciation, and symbols

The difference between one and the other is that when you give credit, you and whoever you’re giving credit to gets to go to the bank.

I came into fashion researching Black history and the further you go back everything vanished into symbols, so I was deeply involved in symbols when I got into fashion. Which symbols was I most fascinated by? It’s a toss-up between Gucci and Versace.

On orthodoxy

There’s no right or wrong in fashion. There’s a weak or strong. And it’s the strong people who come along and determine what fashion is.

On accessories

The scarf and the pocket square is a signal that I use. If you wear the scarf as an ascot, you at a certain level, and you’re in a certain mindset. And if you wear it as a durag, that’s another level. But everything is a reflection of the mindset and all mindsets are important. The reason I wear it this way is a reflection of my generation. I think each generation should be a reflection of who they are.

On where it went wrong

There’s a point in time in hip-hop fashion where we lost it. We lost it when the hip-hop brands came in, they didn’t identify with each individual artist, they went into cookie-cutter street fashion and that changed the flavor of how you interpret the culture, there’s no more individuality. There were these new brands that were emerging and everyone was dressing straight out of the brand.

On that jacket

Everybody knows the Louis Vuitton jacket with the sleeves. That was fashion’s wake up. I’m glad that happened. It was inevitable. Social media made that possible and I’m thankful for that, and I’m thankful to Beyonce for wearing it and for Gucci for using it on the runway and paying homage. That was a significant point.

Throughout history, information has been a great transformer. The whole thirty years that I was underground making luxury fashion, nobody knew but the immediate circle that I was in. What changed all that was social media. When people got the opportunity the connect the fashion to the roots from which it came, that changed everything for me. Once that door opened up and they saw where it was coming from, they couldn’t do anything else but embrace it.

Head over to Sotheby's to learn more about the auction.