NEW YORK, United States — The Apollo Theater is an iconic venue for the African American community. Located in the middle of Harlem, it’s been showcasing artists of colour ever since it rose to fame in the 1920s during the Harlem Renaissance. Artists like Billie Holiday, James Brown, Sammy Davis Jr, Prince and Michael Jackson have graced its stage, as have countless lesser-known artists showcased at the Amateur Night the venue has been hosting for nearly 90 years.

On Sunday night, the Apollo hosted a very different type of performance: Tommy Hilfiger's TommyNow Fall 2019 fashion show during New York Fashion Week, a collection the designer debuted with the actress Zendaya.

Set up outside behind the venue, models wore seventies-styles patterned suits and velvet bell-bottom jumpsuits, and danced enthusiastically down the street-turned-runway to a live band blasting classics like Aretha Franklin’s “Respect” and Curtis Mayfield’s “Move On Up.”

Hilfiger said showing at the Apollo Theater is especially meaningful to him; as a music lover, and as someone who's spent over three decades building a relationship with artists of colour.

“It’s exciting to be showing here because it’s one of the [most] important theatres in the world and I’m proud to stand behind what it represents,” Hilfiger told BoF in a backstage interview before the show. “I feel that we've always been a brand that celebrates diversity and inclusion and that was heightened in the 90s, thanks to hip-hop artists. I’m proud to have been one of the first ones to have worked with them, because back then people didn’t quite get it.”

Although he now has a billion-dollar brand, owned by PVH Corp, it was the hip-hop culture of the 1990s that helped catapult the Tommy Hilfiger label to international success. In today's climate, fashion brands are constantly being scrutinised for how much they prey off of minority group's culture, and profit off of their designs by appropriating them to mass audiences. Hilfiger, being a white designer and taking inspiration from black artists, might have raised concerns of cultural appropriation. But because he built a strong relationship with African American artists, placing them front and centre in his marketing efforts, experts say Hilfiger is an example of someone who has figured out how to navigate the thorny issue of fashion and race.

“Tommy Hilfiger is totally comfortable at the Apollo and that’s because he has credibility with black artists,” said Teri Agins, a veteran fashion reporter and author.

Tommy Hilfiger is totally comfortable at the Apollo and that's because he has credibility with black artists.

In the mid-1980s, when Hilfiger first developed his fashion label, the designer leaned on a specific aesthetic — giant logos and large block letters. Initially, this style was more of a marketing decision than a sartorial choice.

“Tommy leaned towards big, showy logos because he was using it as signage,” said Agins. “He started out as a department store brand, and when you only get a few racks inside a department store, you need clothing that stands out.”

The clothing soon caught on with hip-hop icons. Grand Puba, the rapper from the band Brand Nubian, for example, name-dropped the brand in a song with Mary J. Blige, and began wearing head-to-toe Tommy Hilfiger.

"Tommy Hilfiger and Ralph Lauren prioritised boating and WASP cultural, conveying an aspirational lifestyle and the hip hop community was very impressionable towards that," said Kimberly Jenkins, a professor of fashion history and race at Parsons. "The principle of hip hop music is self-determination, and so getting their hands on precious, sought-after brands like Tommy Hilfiger was tantamount. Even if they didn't fit into the WASP community, they felt like they did by wearing the big logos."

At the time, many European fashion designers knew the hip hop community fancied their clothes, but chose not to work with them.

“Back then, no one wanted to touch the rappers,” Agins said. “They were considered radioactive, and their music was seen as underground.”

But once Hilfiger got wind that the hip hop community liked his designs, he pursued the relationship. He gifted clothing to rappers like Raekwon, Coolio, Russell Simmons and Snoop Dogg, who wore a Tommy Hilfiger rugby shirt while performing on SNL in 1994.

“The rappers loved the clothing because it was showy and cool and very distinctive,” said Agins. “People initially teased Tommy that he was all about the logo, and even warned him that he might be going too black. But once the rappers embraced it, he went with it, and starting to make things more oversized and slouchy, to look like a rapper’s style.”

Back then, no one wanted to touch the rappers. They were considered radioactive, and their music was seen as underground.

Tommy Hilfiger designs also soon began to mimic the rappers' styles. He took cues from other brands that were popular amongst rappers during the '90s; most notably FUBU and Cross Colours, both brands created by black designers. Had Hilfiger debuted these styles today, the fashion press might have pounced on him. But Robin Givhan, The Washington Post's fashion critic, said Hilfiger sidestepped the issue because black artists were the ones who came to him first.

“What gets under people's skin about cultural appropriation is when people take away from those with less power,” said Givhan. “But in the case of Tommy and rappers, it was the less-powerful taking something that objectively belonged to the WASP arena and reimagining it for their own purposes. The rappers were using the Americana stuff that Tommy and Ralph were selling, and by wearing them, said, ‘we are powerful, patriotic, and have arrived on our own terms.’”

Jenkins said the link between hip hop and Tommy never felt exploitative because while Hilfiger was profiting off of black rappers, he also directly looped them into his world. Hilfiger sought out black talent, embracing them in a way that other white designers did not. He cast names like Kidada Jones, Usher and Aaliyah in his advertising campaigns and also mentored artists like Russell Simmons and Sean Combs.

Hilfiger profiting off of black artists isn’t entirely free of backlash. In the late ’90s, a rumour spread that Hilfiger wasn’t happy black people were wearing his clothing — an allegation that followed the designer around through the early aughts until Hilfiger went on “The Oprah Winfrey Show” in 2007 to vehemently dispute the allegations.

Even under that cloud, Hilfiger continued to work on his relationship with black talent, working with names like Tyson Beckford and Beyonce. It’s because of this trail of collaboration, said Jenkins, that the hip hop community felt like Hilfiger was an ally, and still does till this day.

In the case of Tommy and rappers, it was the less-powerful taking something that objectively belonged to the WASP arena and reimagining it for their own purposes.

“At the heart of the matter of cultural appropriation is power, and actually taking something that a culture has developed, and claiming total ownership without profit-sharing,” said Jenkins. “But this isn’t how the community saw Tommy. They embraced each other.”

As an industry that thrives on exclusivity, championing diversity is not something that comes easily to fashion. Yet at the Tommy Hilfiger show at the Apollo Theater, the crowd was noticeably diverse, as were the show’s models.

“A lot of the women modelling tonight have not had as much opportunity as they should have had, and we're happy to give them the opportunity,” Hilfiger said. “It’s a very diverse cast and I love the heart of that type of empowerment.”

The star of the moment, Zendaya, also represents the new guards of fashion and entertainment, which insist on diversity and inclusion.

“For a designer to focus on a millennial, woman of colour [like Zendaya], and put a show on at the Apollo is significant and is a step forward in attempting to bridge the more privileged spaces of fashion that Tommy Hilfiger represents with a community that’s been marginalised from it,” said Jenkins. “It’s a bridge.”