Born on January 28, 1974, Obana grew up in Kanagawa, a coastal prefecture located south of Tokyo. He fell in love with vintage clothes at a young age and eventually dropped out of vocational college to work at Tokyo vintage store Voice: “Vintage and military garments all have a high degree of functionality, and when I started out, I loved restoring the pieces in my collection to their former glory,” he explained to Hypebeast in 2016. In 1995, Obana opened the vintage shop “go-getter,” where his curated selection of ’70s and ’80s designer clothing helped spark trends in Japan.

Yet, Obana was not satisfied with simply selling vintage clothing, and, in 2000, he began designing and making his own garments—including some reworked from vintage materials: “When working in a vintage store I wanted to make clothes with the quality that vintage pieces didn’t have, or create pieces I wished were vintage. That’s how it all started,” Obana told Farfetch. Around the same time, the designer also decided to move to Tokyo, which allowed him to further commit himself to the transition from shop owner to designer: “I must have been about 27 when I moved to Tokyo. It was after I started the brand. Before that, I commuted from my hometown and worked overnight every day for maybe three or four years. It was definitely a good decision; the city provided me with a lot of inspiration and opportunity,” Obana said.

In 2001, Obana officially founded N.Hoolywood, inspired by the location where he often stayed during vintage buying trips to the US and, in fact, the residence’s address—“12960 BOSWORTH ST.N.HOLLYWOOD.CA”—is printed on the underside of the tag on each of his garments. In February of 2002, the designer showed his first collection, Spring/Summer 2002’s “Reclamation,” in Tokyo; for his debut, Obana took oversized garments and cut and crafted them into unusual silhouettes, such as pants with twisted and overlapping fronts. Already attuned to the theatrics of the runway, Obana had the patter of a sewing machine serve as the soundtrack to the collection’s runway show. Not long after, he opened his first Mister Hollywood store in Shibuya to showcase his new brand, naming it after the nickname he developed during his buying trips to the US: “A neighborhood friend of mine in Japan started calling me it. Whenever I’d come back from America, he’d be like ‘It’s Mister Hollywood,’” Obana explained to GQ.

In 2007, Obana launched N.Hoolwyood Compile—a sort of diffusion line that merges unusual fabrics and details with classic silhouettes—during Paris fashion week. In 2008, he opened his first freestanding store in Hong Kong; the same year, Obana saw his brand gain additional traction in the US when New York City’s groundbreaking boutique, Opening Ceremony, announced that, for Fall/Winter 2008, it would feature Japanese designers, including N.Hoolywood. Although Obana had shown his line in Tokyo for five years by then, in retrospect, it’s easy to see that his eye was always on the American market. While his early collections were inspired by his passion for reworking fabrics and garments—as seen in Spring/Summer 2003’s “Medical,” (which utilized materials, such as bandages, not traditionally found in fashion) and Fall/Winter 2003’s “Dress Door” (which merged the technical details of outerwear with the fabrics and silhouettes of eveningwear)—his collections increasingly looked toward American pop culture and history for inspiration.

Starting with Spring/Summer 2004’s “Activist,” which paid homage to Dead Kennedys vocalist Jello Biafra, Obana began to pull from America’s sprawling geography and diverse cultures, including themes such as the urbanization of Alaska and the relationship of pantomime and ’80s hip hop. As the decade came to a close, the designer’s themes became even more explicitly American, as shown by Fall/Winter 2008’s “Daily Life Truth,”—inspired by Harvey Pekar’s graphic novel “American Splendor”—and Spring/Summer 2009’s “New Order,” inspired by Amish quilts.

So, it wasn’t necessarily a surprise when, in 2010, Obana announced that he was making the move to New York Fashion Week not only because of the influence of American clothing on his designs, but to also get out of his comfort zone: “The same Japanese editors were just saying the same things, always complimenting me. I wanted different comments and judgements,” he explained to Highsnobiety in 2015. Obana was also looking to attract the interest of American companies in the hopes of landing a similar position to that of Daiki Suzuki, who had recently stepped down from his five-year stint as head designer of American outdoor clothier Woolrich’s upmarket Woolrich Woolen Mills line: “Honestly, I’d love to get an offer from an American label to design. I think I’m an excellent candidate to understand these brands, I’m an American brand geek!” Obana recounted to GQ in 2012.

Obana’s first collection shown in New York was indicative of his tendency to push boundaries; Spring/Summer 2011’s theme, “Police Picture,” drew its inspiration from early-to-mid 20th century mug shots. Although the collection received favorable press, it might have experienced a far different reception had it been designed just a few years later, as police brutality and the prison industrial complex became more common within the lexicon of the mass media. For the next seven seasons, Obana would stick to less controversial American themes—Ernest Hemingway, Amelia Earhart and Yosemite mountaineers, to name a few—while cohesively integrating technical and formal garments and demonstrating an acute eye for fabric and pattern; in fact, the designer stuck to this formula for all but one of his collections, Spring/Summer 2013’s graffiti-inspired “Vandalegal,” which oriented itself closer streetwear and received tepid reviews from outlets like Vogue.

Obana’s brand would, however, see a significant shift for Spring/Summer 2015, as the designer looked to his personal life for inspiration and shifted toward the more casual garments (especially hoodies, bombers and T-shirts) and relaxed silhouettes that have helped define N.Hoolywood’s aesthetics over the past four years. The collection, inspired by his son’s fascination with insects, also reflected Obana’s personal shift in style: “I stopped wearing button-ups two years ago. [I only] wear T-shirts or sweatshirts,” the designer confessed to Highsnobiety in 2015.

Considering Obana’s move toward looser silhouettes, fascination with American archetypes and commitment to fully immersing himself in his concepts, Fall/Winter 2017’s collection inspired by “street people” (almost) makes sense: “Often my desire to express a theme is so strong I end up making ‘works of art’ rather than wearable pieces. We present collections twice a year, but I’ll always be adding little tweaks. If I start to feel sick of it, I think ‘That’s it! The end!’ but we continuously review our work to change and progress,” he explained to Farfetch. Yet, understanding how Obana arrived at drawing aesthetic inspiration from the practical needs of human beings without homes does not excuse the insensitivity of the aforementioned collection. Despite receiving a pass from the show’s attendees and even some critics, it was derided by media outlets such as Fashionista and Refinery29 as the literal manifestation of Mugatu’s “Derelicte” collection from Zoolander. And, while fashion designers have long looked toward the less fortunate for inspiration—Obana’s collection is one of the more egregious examples to date.

Luckily for Obana, the seasonal nature of fashion and his thematic approach to design have resulted in a quick recovery for N.Hoolywood, which appears to be healthier than ever. The brand recently opened its fifth store in Japan and Obana appears to be moving ever closer to his goal of overseeing design for an American label. In 2017, he teamed up with sought-after screen print shop and brand LQQK studio (the two previously collaborated on a Tokyo pop-up shop in 2015) on a denim-centric capsule collection: “I’ve always been friends with Alex of LQQK Studio, so collaborating with them was a very logical next step,” he told Hypebeast in 2016. Most recently, Timberland tapped Obana to create a Fall/Winter 2018 capsule collection for its Pro line; the collaboration so consumed the designer’s headspace that it informed his own workwear-inspired collection (which featured additional collaborations with Lee and Converse Addict). In a reversal from two seasons prior, Obana’s collection received near-universal praise; in fact, even as The Washington Post critiqued “fashion’s obsession with working-man style,” it commended how the designer’s clothes “exuded a rugged urbanity that was elevated by the designer’s eye for proportions.”

Will Obana stay in the good graces of the American media and land a head designer role at an American brand that he so covets? Does he simply have his finger on the pulse of the country’s sociopolitical issues, or is he culturally incompetent? Considering the designer’s coyness regarding interviews and his conceptual approach to design, the direction of his brand is near-impossible to predict. “I focus on what I want to do, not what other people like,” Obana told Hypebeast earlier this year. What is clear is that Obana’s singular vision adds significantly to the ongoing conversation between American and Japanese fashion design and that both would be far less interesting without him.