From Yacht Clubs To Lil Yachty: The History Of Nautica And Hip-Hop

The story of how Nautica, a clothing company which self-describes as “a leading water-inspired global lifestyle brand,” earned its place in the hip-hop fashion canon is hard to track down. At first glance, there appears to be no explanation at all for how the brand, founded in 1983 by a Taiwanese immigrant named David Chu and marketed exclusively to white people with boats, ended up on the the bodies –- and in the lyrics –- of the likes of Nas, Lil Kim, and Wu Tang Clan by the mid-90s.

Nautica is best known for its use of bold primary and secondary colors, its swooping wordmark, boat prints, and general seafaring vibe. Jordan Page, a Brooklyn-based vintage archivist and stylist commented on the brand’s clean, bold look. “When I think of Nautica I think of that big, bold Nautica font,” he said. “Classic jackets and knit sweaters with big logos. The colors never got too crazy, and everything was always in a good, clean line.” Their brand was and continues to be strongly American, in the most stereotypical sense: “You saw it in the ad campaigns,” Page continued. “Handsome white men with white women, very rich in appearance, smiling.”

Alongside Polo Ralph Lauren and Tommy Hilfiger, Nautica was one third of the holy trinity of luxury-casual Americana brands in the 1990s. “Nautica was the baby brother,” Page recalled. “It didn’t hit as hard as the other two brands, but its presence was felt.”

What set Nautica apart was its specificity. While Polo and Tommy embraced America-as-brand more literally, often incorporating the letters “USA,” or the flag and its palette into their garments, Nautica stuck true to its water-centric mission. In addition to the boat icons adorning every piece, often printed oversize on the backs of their signature windbreakers, many pieces included specific nautical references –- flags from historical yacht races, for example, or the geographical coordinates of their finish lines. The J-Class series of jackets, widely considered Nautica’s most iconic collection, is named after the vessel classification of that peak yacht-racing era, and have “1930 1937” printed on their chests and sleeves –- the only years in which J-Class yachts were manufactured.

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Nautica Flavors #comingsoon #3rdeyevintage

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The specificity of its mission, marketing, and target demographic is what differentiated Nautica from its competitors. It had the same preppy aesthetic and quality build as its peers, but was distinguished by its origin and iconography. That eccentricity is what allowed it to compete on the level of Polo, a much older, larger, and more established brand, within a decade of its inception. It was also an important part of the appeal outside of its target wealthy white demographic. As Emeka Obi, a Creative Strategist who grew up in Brooklyn’s East New York noted, Nautica signified a level of prestige that was deeply appealing. “If I’m wearing Polo, people will think of me as someone who can afford Polo, that I’m not like any of the other dudes on my block,” Obi said. “It’s socially aspirational -– you want to be seen as somebody who’s been to the Hamptons, even though you’ve never left the Bronx.”

“Nautica was a representation of a specific part of white America that most Black Americans didn’t know about or understand,” Page further explained. Rather than putting people off, the boat-theme was its appeal. “That’s how the fascination started,” Page said, echoing Obi. “It was aspirational –- wearing these clothes made black people feel like they were a part of that community.”

Though Nautica and its peers were established players in the luxury market by the late 1980s, their adoption in the urban market didn’t begin until 1992. Up to that point, European fashion houses like Gucci, Louis Vuitton, and Yves St. Laurent ran the game. These brands were scarce and expensive, which made them all the more desirable.

For the decade preceding the ascent of Polo, Tommy, and Nautica, the main supplier of European luxury garments for black people in New York City was a man named Daniel Day, better known as Dapper Dan. At his boutique on 125th street in Harlem, he custom tailored and retrofitted designs from the likes of Fendi, Dior, and Louis Vuitton to suit his black clientele. He’d dissect imported pieces from their collections and rebuild them as custom outfits for clients like LL Cool J, Mike Tyson, and Big Daddy Kane, maximizing the garments’ gaudiness by screen-printing additional logos all over them. He called this process “blackenizing,” and referred to his creations as “knock-ups” rather than knock-offs, because they were, in fact, made from the real thing.

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'88 attire. #dapperdan #harlem

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Dapper Dan’s creations were painstakingly made by hand from already rare and expensive source material, and it was impossible to keep up with the demand. Day has famously claimed to have been awake and at work in his boutique 24-hours a day for eight years straight. He kept the gate up part-way at night, in case a rapper showed up in need of a fresh look. Still, he credits his downfall not to his limited production capacity but to MTV’s contemporary practice of censoring brand logos in music videos: His clothes were saturated with insignia, meaning Eric B. and Rakim’s heads would appear floating atop their entirely blurred-out bodies on Yo! MTV Raps.

While a select few of Dapper Dan’s customers could pick up authentic luxury pieces overseas, most who could afford it were limited to what was available at the Gucci and YSL boutiques in Manhattan, which primarily sold accessories like wallets and handbags. When his boutique was raided by the FBI for copyright infringement and eventually shuttered in 1992, there was no one to fill that void.

In hindsight, it seems logical that, at the time, the most likely candidates to replace European luxury brands in the urban market were the newly founded black-owned fashion lines. Starting in 1989, designers and entrepreneurs like Carl Jones, Karl Kani, and Russell Simmons were looking to take the reigns of the urban fashion, and rightfully so, as its cultural pioneers. Though brands like Cross Colours, Phat Farm, and FUBU made a strong play for the market, they lacked the high-end appeal of their European forebearers. “Once people start learning that things were made for them, they just don’t want them anymore,” Obi reflected. These brands failed to capture the top-slots in the market specifically because they were designed to.

In the tradition of the Dapper Dan-era, wearing the brands that were beyond the means of your peers was the ultimate display of class. “If you wanted the good stuff, you couldn’t get it at Macy’s,” Obi said. “You had to travel outside of your neighborhood, go to Bloomingdale’s. It signified that you’re a little bit more worldly than your peers.” As had been the case with the European brands, the labels on your body were the key to your identity, and desirability was driven by scarcity.

“It was an economy of people living and dying by whatever the hottest thing was out,” Obi said. “Brands who came out of and marketed to the urban sector had a hard time -– no one feels like they want to be marketed to.” As a result, the best-dressed people in the hood weren’t wearing FUBU, in spite of its organic relationship the market. Instead, luxury department store brands were perfectly positioned to occupy that vacancy on the high-end. Enter Polo, Hilfiger, and Nautica.

Spurred by their status as rare but not impossible to come by, the thirst for these brands spread quickly. The brands perpetuated demand by releasing different pieces and collections in different regions, meaning you either had to travel to get the best, rarest items, or you had to trade up for them. Each brand had its loyalists, though Polo was the most popular as well as the most diversified, with its many sub-labels. Kids in Brooklyn built their identities around their collections and formed gangs based on their brands of preference -– the Lo-Life Crew, Tommy’s Kids. “Boosting” or stealing from Bloomingdale’s and brand outlets was a way of life for these gangs, as was robbing the gear straight off the bodies of unsuspecting strangers.

“My nextdoor neighbor was a Lo-Life,” Obi recalled. “He would steal from Bloomingdale’s and give me stuff because we were good friends. Then I would trade up. I was able to get myself a formidable collection of Polo, and then I begged my mother to get me a Nautica jacket for Christmas — I was invincible with that Nautica goose.”

Confirming Obi’s account, Page recounted: “A Nautica jacket, a pair of Timberlands and a Playstation. That’s what you wanted for Christmas in 1995.”

The frenzy was at its peak from 1994 to ‘97. While Nautica remained the smallest, most niche of the three brands, its significance as the wildcard among them was undeniable. “They were pushing for that Ivy League, white-bread customer, but their shit had giant boats on it,” laughed Obi. “It was graphic, it was big. The more covetable stuff was was the all-over-prints, the reversibles, things with nautical terms, numbers and knot-speeds, geographical locationing on it.” Essentially, the weirder, more out-of-context a piece would appear on the streets of Brooklyn, the better.

The contextually-bizarre technical seafaring functionality of the Nautica Competition and Challenge lines — which wereintroduced during this period — increased the desirability of those garments. “At the time, technical-wear was really big,” Obi said. “The more tech your thing looked the more prone somebody was to get it. Anything with some opposable strap that meant nothing or buckle that had no purpose, a fastener that was overly complicated. Things like that were huge.”

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Sittin on top of fitty grand in a Nautica van, Uh!

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Perhaps a warped extension of the reign of performance-wear in the 80s, the coveting of superfluous ”functionalism” was present across the urban market, particularly in footwear. Consider LA Lights, Reebok Pumps, and the overly-strappy Jordan 8s. “I’ve never seen somebody play basketball in a pair of Jordan 8s,” Obi joked, but that didn’t stop people from buying them. In fact, their impracticality was, in a way, their selling point. Likewise, Nautica’s flair for flamboyant-functionality boosted its influence and desirability among those big three brands.

Unfortunately for Nautica, its heyday was short-lived. The specificity that differentiated the brand from its peers is also what precipitated its downfall. “They didn’t really step outside of the whole ‘we love boats’ thing,” Obi said. “The gear just kind of became straightforward. By the late 90s, they didn’t really do the more outlandish stuff that they were doing previously, so they didn’t stand out in the market.” They were late to the game when it came to differentiating their offerings, and their sub-labels lacked the diversity of collections like Polo Sport or Cold Wave.

By the late 90s, a second wave of black-owned urban brands emerged. Unlike in 1992, when black designers failed to capture the high-end urban market, Sean John and Rocawear were overnight successes, propelled by the celebrity status of the rappers behind them. They went straight to the department stores, courting a white audience from the jump, and brought the FUBUs and the Phat Farms along with them. Hip-Hop was newly mainstream, and Diddy’s approach to high fashion in the urban space resonated across cultural boundaries, eroding the market share of the luxury department store brands that came before him.

Around the new millennium, sales declined across the board and Polo, Nautica, and Tommy found themselves edged out of the urban market. Hilfiger, in spending the better part of the ’90s pandering to his newfound hip-hop audience, had alienated his core business. Ralph Lauren fell back on its original customer-base with the classic Polo shirt business, while Nautica struggled to regain footing. “They didn’t have the legacy that Polo had,” Obi noted. “Polo has been recognized as a brand since the mid 1960s, but Nautica didn’t get that recognition until the mid 90s.”

One of Nautica’s drawbacks during that time may have been their decision to tie the brand to a specific concept rather than a figurehead. Unlike Lauren and Hilfiger, whose faces remain synonymous with their respective brands to this day, David Chu was never the face of Nautica. “No one knew who David Chu was or what he looked like, no one referenced him in hip-hop lyrics,” Page explained. “Nautica stood alone because there wasn’t a marquee figure to represent the brand.” Rather than hiring someone to fill that role, Nautica stuck to the same marketing tactics, featuring anonymous white people on the water. It was a testament to the brand’s failure to adapt, and made it even harder to diversify its offerings. While Lauren and Hilfiger could use themselves to maintain continuity in their brands while switching up their styles, Nautica had no such flexibility, and suffered for a time because of that.

In 2003, David Chu sold Nautica to VF Corporation, the apparel conglomerate home to Timberland, Lee, and The North Face, for a billion dollars. “Once Chu sold it, it lost all identity,” recalled Obi. “With no central iconic figure, there’s no identity.” In the years since, Nautica’s endured a quiet return to form. Basic swimwear, t-shirts, perfumes and sunglasses have been made up its core business.

Though its significance is undisputed by the people who were alive at the time, there is little evidence of Nautica’s history in urban fashion. Unlike Polo and Tommy, there are no books or listicles about it, no vintage ad campaigns featuring black artists or images of its founder flanked by rappers. In time, it likely would have been forgotten altogether had it not gained a new, unlikely champion last year when Atlanta newcomer Lil Yachty burst onto the scene, dressed head-to-toe in vintage Nautica digs.

It appeared almost as if he’d designed his persona around the brand, but in fact even Yachty was unaware of Nautica’s history in urban fashion at first. When I spoke to him about it, he admitted that he wasn’t familiar with the brand until he’d already adopted his moniker and his signature buoy-esque beaded red braids. “I got my name from a group called the Yacht Club,” he told me. “My old manager put me on to Nautica because of my name, like, ‘Hey man it’d be cool if you did something with this.’ I was drawn to how different it was, I just love doing stuff that other people aren’t doing. I started collecting it from everywhere. Thrift stores, vintage shops, online. It wasn’t a planned thing, I just wore it and it became my thing.”

It turned out to be a serendipitous branding opportunity. “I always tag them on social media so I guess I stuck on their radar,” he said. “They started following me.” Less than a year later, Nautica is poised to launch its debut throwback collection with Urban Outfitters, with Yachty as the face of the campaign. The collection is extremely true to their signature mid-90s styles, acutely positioning the brand for a return to the cultural conversation by highlighting the importance of its hip-hop heritage. After decades of all but ignoring its history with black fashion, the brand seems to be smartening up to its potential to be capitalized on.

Lil Yachty is the first black face of a Nautica campaign; the brand came knocking after he’d given them a year of nearly constant free promotion. But he doesn’t seem salty about it. “I guess they realized I was the perfect person for this launch. It’s dope,” he said, palpably excited about the collaboration. “I’m glad they’re finally paying attention to how popular the old collections were. I’m looking forward to more collections, more collaborations.” Those interested can now shop the collection here.

A few days before the new collection was announced, Yachty posted an Instagram of himself getting kissed on the cheek by Karen Murray, the President of Sportswear at VF who oversees the Nautica brand, with the caption “New Bae.” If Yachty’s enthusiasm does drive additional collections, perhaps even with his creative input, Nautica might just have found their long-needed voice. If not for Yachty’s influence, the resurgence of ‘90s fashion over the past few years could easily have ended up excluding Nautica entirely. Instead, it’s created the perfect opportunity for their re-entry to the market. While this capsule collection marks a turning point, it remains to be seen whether Nautica will leverage this opening to make a full blown comeback in the urban market.

Ezra Glenn is a freelance writer and brand strategist in Brooklyn. Follow him on Twitter and Instagram.