In 1979, he decided to settle more permanently in Laguna Beach and establish a business making surfboards. For the twenty-four-year-old Stüssy, what may have felt like an insignificant life decision paid off almost immediately. While still working for Russell Surfboards—and inspired by the Punk aesthetics of the Sex Pistols and The Clash, who had only recently found an audience in the US—Stüssy started signing “shape S Stüssy” on his boards, despite the disapproval of his hippie coworkers. Now, free from Russell, he decided to take it a step further, tagging his name in thick black marker as a “fuck you” and self-declaration, like the many young graffiti artists hitting subway cars in New York City at the time.

In 1981-’82, he was offered a small table at the Action Sports Retailer trade show in Long Beach to highlight surfboard making. On a whim, Stüssy decided to screen-print his tag in white on a bunch of black Hanes t-shirts. After three days at the trade show, his boards had sold relatively well, but his t-shirts are what people were buzzing about: “every single person came by saying: ‘Yeah I’ll take a board or I’ll take two boards, but how much are those t-shirts? […] So I was like, ‘Okay, they’re eight bucks,’ or I forget,” Stüssy recounted to Empire Ave in a rare 2013 interview. After selling roughly one thousand tees, the now fledgling designer went home to print the shirts and had a near-epiphany: “…I’m shaping one board a day…you know how Merrick’s shaping five a day and I was like a ’60s hippie still, like fuck you production guys […] it was like my art, you know? […] Then, I’m like oh now I can put food on the table with these tee shirt things.”

At the next trade show six months later, Stüssy arrived with two t-shirt styles, but his customers again were drawn to an item he hadn’t made to sell. Stüssy had tired of the “little cord OP short shorts” most surfers wore at the time and, following the punk influence that was currently driving his style, bought Vietnam military chinos from an Army Navy and had his mom cut them off about three inches above the knee. These shorts elicited such excitement from the surfers at the trade show that Stüssy decided to make a hundred pairs once he got home: “Yeah, so we took shopping bags, like I would take from the grocery store, the brown square bags and I made a template. And so then my mom and my aunt made a hundred pairs. It was never like I’m going to start a clothing line,” he told Empire Ave in the same 2013 interview.

Although in the early 1980’s, Stüssy was starting to have success with his improvised designs, he wasn’t necessarily set up to run a sustainable brand. Enter Frank Sinatra, Jr. (either a childhood surf buddy or a fellow skier that Stüssy met at Mammoth Mountain—depending on the account), a certified accountant who believed in the brash young designer’s vision. Sinatra had the business acumen to turn a couple of t-shirts and a pair of shorts into a fully-fledged fashion line. Sinatra offered Stüssy $5,000 to become his partner and, in 1984, they officially established Stüssy, Inc., eventually registering the company’s trademark in 1986.

The brand’s first designs were work wear-influenced and logo-driven; these include the now classic, Chanel-inspired “Stüssy No. 4” and interlocking double S, as well as the bold S design that was affixed to baseball and painters caps, which, according to Sinatra, Stüssy had seen cool kids wearing and saw as “a great vehicle for fashion.” These visual references to high-fashion acted as proclamations of Stüssy’s relevance and owe much to the rise of remix culture proliferated by early ’80s hip-hop and graffiti artists, whether it be Son 1 and Rem’s 1983 “Donkey Kong and Mario” sprayed on a subway car in NYC or Run-D.M.C.’s sampling of The Knack’s 1979 hit, “My Sharona” for their song, “It’s Tricky” off of 1986’s Raising Hell.

Speaking of Raising Hell, it’s no accident that Stüssy began to gain national footing the same year that Run-D.M.C. dropped “My Adidas” and put a stranglehold on hip-hop, ushering in a harder sound and toned-down aesthetics. In a 2012 interview with Complex, Sinatra explained the sudden change the brand saw in the market in ’86: “From 1980 to 1985, Stüssy was being drowned out by all the loud, over-the-top products being sold everywhere. By ’86, customers were tired of dressing in all that flash. We found ourselves at the beginning of this streetwear trend when some of the more forward-looking customers started looking for clothes that they could wear at night—to the club—instead of a day at the beach.”

By 1987, the marketed had shifted so far in Stüssy’s direction that the brand moved into a 4,000-square-foot office in Irvine, California; in ’88, Stüssy released its clothing in Europe; and, by the end of the decade, the brand had stockists throughout the US, Europe, and even Australia and Japan. Despite increased sales, Stüssy and Sinatra maintained the allure and authenticity of their brand by refusing investors and choosing to sell to select shops. Stüssy’s increased sales also allowed the designer to travel throughout Europe and Asia, partying in nightclubs and making connections with other young creatives like Hiroshi Fujiwara, Jules Gayton, Alex “Baby” Turnbull, and Michael Koppelman.

This grassroots approach continued into the early 1990’s as Stüssy and Sinatra further expanded the reach of their brand through collaborations, pop cultural engagement, and the creation of the IST (International Stüssy Tribe) that helped spread their gospel. In 1990, Stüssy created cover art for Vivienne Westwood’s former boyfriend and early hip-hop appropriator, Malcolm McLaren’s album, Round the Outside! Round the Outside!. This collaboration is a perfect microcosm of the way Stüssy was able to cultivate relationships with worldwide tastemakers to increase his brand’s visibility. McLaren had already helped Westwood turn punk style into high-fashion in the ’70’s through their World’s End shop in London before setting his sights on the burgeoning hip-hop movement in New York City and collaborating with The World Famous Supreme Team, among others, on 1983’s Duck Rock. Despite some hip-hop purists’ distaste for McLaren, he—and people like him—knew how create broader audiences for subcultural movements; the simple act of having Stüssy’s signature artwork on McLaren’s newest project helped connect the brand to some of the most relevant art, music, and fashion of time.

1990 was big, but ’91 was an even bigger year for Stüssy. It marked the first International Stüssy Tribe meeting, which took place in Tokyo, Japan, as well as the opening of the brand’s first stand-alone store—a collaborative project with James Jebbia (pre-Supreme fame)—which opened in a 900 square foot space at 104 Prince Street in SoHo in November. Jebbia had opened Union with his partner, Mary Ann Fusco, in ’89, but the shop mostly carried younger British brands and was only able to stock Stüssy after the man himself visited the store and deemed it worthy.

By ’91, many of the young creatives Stüssy had met during his travels, such as the aforementioned Fujiwara, Gayton, Turnbull, and Koppelman—who, with his partner Miles Siggens, took over UK distribution for the brand—were part of the IST. The first official meeting in Tokyo was a chance to bring all these members together and solidify the brand’s creative community. As Gayton recounted to Complex: “They flew us all out there. There was the London Tribe. There was the New York tribe. And we all met up in Tokyo with Hiroshi and all the Japanese tribe and had this big party. Me, Alex and Hiroshi DJed. So that was where it turned international.” Stüssy and Sinatra also made up commemorative IST branded varsity jackets for the meeting, each emblazoned with that particular member’s nickname, which acted as another level of marketing that carried over from the event.

In 1992, the brand grew again, opening The Stüssy Union on La Brea in Los Angeles; the store was split into two sides, one for Stüssy and one for all the brands Union carried in New York. Eddie Cruz—who Jebbia tapped to run Union in NYC after he opened the first Stüssy store—moved out to California to oversee the shop. (Cruz, of course, would later go on to found the brand Undefeated). Eventually, Stüssy grew to the point where Cruz moved Union’s brands out, turning the divided-store into two stand-alone shops. Stüssy continued its expansion through the mid-'90s, opening shops in Laguna Beach and Tokyo, gaining stockists in Europe and Japan, and even coming to a licensing agreement with Australian designers, Felicity Rulikowski and Bernadette Wier, to start Stüssy Sista Gear, a twenty-five piece collection made for women and sold exclusively in Australia and Stüssy’s stores.

Then, in 1996, seemingly out of nowhere, Stüssy fell hard. Throughout ’95 there had been rumors that Stüssy was unhappy with the direction of his brand. From the beginning, he had cared more about creativity than turning a large profit, and it’s easy to imagine that this perspective clashed with Sinatra’s business-minded approach. In January of ’96, Stüssy made it official and resigned as president of the company; he initially agreed to stay on as a consultant and run the New York and LA boutiques, but eventually sold his shares to Sinatra and made his departure complete.

Beyond losing its founder and designer, Stüssy was struggling in other ways. Competitors like Mossimo were biting the brand’s designs and selling to a broader market, thereby diluting Stüssy’s image. With new urban wear brands beginning to gain market share—like Russell Simmon’s Phat Farm—and define “streetwear” for a new era, there was a greater appeal flashier consumer tastes. Even the profit-conscious Sinatra had no desire to go in the direction of the aesthetics propagated by many rappers of the era (à la Puffy and Ma$e’s shiny suits in the video for ‘97’s “Mo’ Money Mo’ Problems”). The mid-to-late-'90s were the rare period when Stüssy missed the pulse of hip-hop, and intentionally so; instead of following the trends of the day, Sinatra decided to turn Stüssy’s focus away from the US and toward the twenty to thirty loyal European and Japanese accounts the brand had built over the past ten years.

Then, in ’99, Stüssy found a way to reestablish itself in the US. Photographer Robbie Jeffers pitched Sinatra on starting a skateboarding team. With Sinatra’s blessing, Jeffers reached out to Richard Mulder in December of that year, and, by 2000, the brand boasted a skate team comprised of Richard Mulder, Danny Montoya, Scott Johnson, Keith Hufnagel (who would go on to found HUF), and Chad Timtim, with Jeffers as the manger. Skaters Anthony Van Engelen, Justin Eldridge, Justin Reynolds and Danny Supa joined the ranks for stints at various points as well. That same year, Stüssy sponsored a skate tour of Tokyo and London; Nike, which was starting to take a greater interest in street, skate, and sneaker culture, took notice. Stüssy’s longtime distributor in the UK, Koppelman (who would go on to found Footpatrol, among other projects) brokered a meeting between Stüssy and Nike’s UK marketing team, namely Fraser Cooke, which lead to the 2000 release of two exclusive colorways of Nike’s Air Huarache LE at Stüssy London shop.

The following year solidified Stüssy’s reemergence. The brand released its first official collaboration with Nike: two colorways of the Nike Dunk High released exclusively at Stüssy’s stores in New York, London, Tokyo, and Los Angeles and “limited to one purchase per day of the available 24 pairs stocked in each store per day (12 black and 12 brown),” according to the brand’s website. Additionally, by June of ’01 Jeffers was on a yearly contract with the nascent Nike SB, giving additional buzz to the skate team he was simultaneously managing for Stüssy.

Amazingly, Stüssy has maintained its relevance ever since. There were unverified rumors of Sinatra selling the company to Diesel founder Renzo Rosso in the early 2000’s and Stüssy has cycled through a handful of creative directors (namely Paul Mittleman) and head designers (Nick Bower and currently Nin Truong of Maiden Noir), but none of this has prevented the brand from increasing its sales and hype over the years. In fact, the only drama has come in the form of occasional spats between Stüssy and his former brand, which continues to use his artwork from thirty years ago. In 2008, Stüssy founded his new project, S/Double (a nickname that a girlfriend gave him inspired by rapper Erick Sermon’s alias, E-Double-E) and doesn’t seem to appreciate competing against his own artwork and original branding. Between 2011 and 2013, S/Double opened shops in Montecito, California, Tokyo, and Fukuoka, and collaborated with Porter and Reigning Champ, among others, but Stüssy’s brand has been relatively quiet since. And it seems that the man who left his namesake brand over twenty years ago may want it that way. After all, Stüssy only started making clothing in the first place to fund his art.

However, despite the aforementioned grumbles from Stüssy the man, Stüssy the brand continues to make itself relevant in familiar ways. With nearly four decades of building careers for IST members throughout various parts of the fashion industry, Sinatra’s company has shaped a generation of tastemakers that reference Stüssy as a touchstone, meaning the brand has a steady list of spokespeople to champion it and new and old collaborators to choose from. This year alone Stüssy has collaborated with Vans, Bedwin & the Heartbreakers, and Hypnotize Hearts on clothing; produced a short film with Jared Sherbert and a photo editorial with Tyrone Lebon; and opened a new flagship store in Toronto. If Shawn Stüssy were still on board, it might as well be 1991.