Sternberg’s interest in clothing quickly led him to visualizing his own concept: “I put together my inspiration boards, I hired a student to draw some flats for me so there were garments in there. I had fabric swatches, I did a proper collection pitch, and I made a proper presentation of it,” Sternberg explained to the Chicago Tribune. Emily Woods responded to this pitch, telling Sternberg, “Listen, you have no training but your ideas are lucid — you couldn't be more clear. This is what a fashion designer is. Have you ever thought about doing this? It seems so natural to you.” In October of 2003, Sternberg left Wood’s company and took classes in illustration, pattern-making and garment construction. In January of 2004, he launched Band of Outsiders.

Sternberg launched Band of Outsiders in Los Angeles, a risky decision at the time. While Los Angeles’ burgeoning fashion scene has gained a bout of clout in the past couple years, back in the early 2000s, setting up an American label away from the established fashion capital of NYC was a risk. Sternberg desired to produce most of his clothing in Italy, a sixteen-hour flight and nine-hour time difference from California. Furthermore, the city’s lack of fashion culture and infrastructure made it difficult to recruit designers and for the brand. Yet, Sternberg appreciated the opportunity to work outside the fashion dialogue, helping him build the brand’s singularity (and tie it even further to Band’s cinematic inspirations).

Band of Outsiders was named after the classic French new wave film, Bande à Part, by Jean-Luc Godard. In addition to liking the name sonically, Sternberg saw the name as fitting, simply because it represented his approach to fashion; the retro aesthetic that defined Band of Outsiders allowed it to exist outside of a need to follow runway trends. At its launch, Band of Outsiders solely produced men’s dress shirts and neckties. The small operation saw quick success, being featured at major department stores, such as Barneys New York, within its first year.

With his early success, Sternberg took the opportunity to expand Band of Outsiders. He began developing more menswear, including blazers and pants to pair with his shirts and neckties. In an interview with Bloomberg, Sternberg described Band of Outsiders: “The line is not for a ‘fashion’ person… The customer is either vibing on the cultural references or has this system of preppy dressing that, once you’re a proponent of that, you stick with it.” Sternberg did not hope to make avant-garde clothing, and Band’s most loyal customers loved the line’s simplicity and consistent charm. Within its first three years, the menswear brand developed a cult-like following young men in their mid-’20s who appreciate fine craftsmanship desperately wanted a nice, classic garments that would fit them—all with a genuine sense of cheekiness and humor.

In 2007, Sternberg’s vision and ambition led him to launch Band of Outsiders women’s line, “Boy.” As an economics major, Sternberg recognized the potential to generate more revenue in the women’s market than the men’s market. Sternberg’s vision for Boy stemmed from his belief that there is nothing cooler than women in men’s clothing and that every woman should own “a beautifully constructed blazer.” Boy continued to release new menswear inspired womenswear each season, up until the brand’s first closing.
Band of Outsiders’ continued success was further catapulted in 2008, when Sternberg won the CFDA award for Emerging Menswear Designer of the Year. The award assisted Sternberg in building connections in the industry: the most notable one with Anna Wintour, who made regular appearances at Band of Outsiders runway shows. Still benefiting from buzz of his 2008 award, Sternberg received (in a tie) the CFDA Menswear Designer of the Year award in 2009, putting him and Band of Outsiders at the forefront of the fashion industry.

In the fall of 2008, Sternberg, who desired to expand the buzz around Band of Outsiders, began a very successful, low-cost Polaroid advertisement campaign. This campaign featured Polaroid pictures taken by Sternberg (who received a minor in photography in college) of celebrities in the brand’s clothing. Inevitably becoming a signature of the brand, Sternberg would go on to feature Michelle Williams, Sarah Silverman and Andrew Garfield in his Band of Outsiders Polaroid campaigns. These campaigns, along with other celebrity endorsements, transformed Band of Outsiders from a respected yet obscure brand to a household name. In later years, the Polaroid campaign featured celebrities Spike Jonze, Dave Franco, Josh Brolin, Amy Adams and Frank Ocean.

Outside of the official Polaroid ad campaigns, there’s very few celebrity Band fans that can top Kanye West. West was a notable front row figure at Band of Outsiders fashion shows and wore one of the brand’s white dinner jackets to both public events and in his Spike Jonze-directed We Were Once a Fairytale 2009 short film. Without question, the gray suits Kanye wore during the 808s & Heartbreak-era were inspired by, and often actually, Band of Outsiders. Take it from the man himself: "Scott's the best," Kanye told the New York Observer after Band's Fall/Winter 2009 show.

Band of Outsiders’ newfound popularity and publicity led to several impressive collaborations. In 2008, the Band started a collection with Sperry Top-Siders. The collaboration was another play to Sternberg’s vision: tweaking and perfecting men’s American prep-wear. The collections, which lasted for five years, featured the popular Sperry boat shoe with stripes, patterns and patchwork. Band of Outsiders also began an impressive partnership with Barneys called “No Bunk, No Junk,” named after a slogan found on a vintage Barneys matchbook label. Sternberg’s purpose behind the collaboration was “about tapping into Barneys’ heritage,” bringing great fashion to Manhattan, while creating “something that’s not Euro, not too slick.” Band of Outsiders used their collaborations to continue growing, while maintaining their core designs.

By 2010, the brand that six years ago solely produced men’s shirts and ties had become a 12 million dollar business that spawned full men’s and women’s collections, along with a few collaborations. Sternberg desired to grow the brand to a 40 million dollar business by expanding their women’s line and tapping into the European market. Band of Outsiders struggled entering the European market, especially in finding local, European-based tailors who could create garments that rivaled those being produced in Brooklyn by legendary suiting master Martin Greenfield (his work with Band's tailored garments were a fixture of Band of Outsiders from 2007 onward). Although holding a similar price point to brands major designer labels, Band of Outsiders garments appeared too basic to Europeans who stylistically preferred slick and chic over handmade and comfortable. The classic-meets-niche appeal that helped Band of Outsiders gain a cult following is exactly what made it difficult to compete; Band of Outsiders had delivered on its commitment to quality, but that came at a higher cost. Unfortunately, shoppers were unwilling to shell out maison-level cash for classic American sportswear when it was so readily available (and more importantly, cheaper) at a myriad of other retailers.

Even with little initial success in the women’s and European market, Band of Outsiders was a pioneer within the preppy menswear industry. The slim-fitting casual button down (Band’s shirts could be loosely compared to the super-slim and shrunken American-inspired tailoring of Thom Browne) became a must have for many men.

With growth in its sights and famous friends supporting the label back at home, Sternberg was invited to take his show on the road, showing as the guest designer at the 80th iteration of Pitti Uomo in Florence. With his Spring/Summer 2012 men’s collection, along with his “Boy” and “Girl” lines, on display, Sternberg utilized the festival’s grandoise potentional to stage a show that was part runway show, part Broadway homage.

While at its start, Band of Outsiders saw its consumer base grow because of its unique take on menswear, its growth began to slow down around 2011. Brands like J. Crew, Polo and Brooks Brothers finally caught up with contemporary (see: slim-tailored) tastes, eventually mass-producing Band of Outsiders-styled button downs that sold for a fraction of the cost. While more men desired Band’s brand of accessible offbeat tailoring, very few cared deeply enough about the artisanal craftsmanship to pay an extra—say $200 or $300—per shirt over something they could inevitably purchase at their local J. Crew (or for more upscale tastes, modern mainstay Steven Alan). In the end, it was a perception that Band of Outsiders was too expensive for what it was that would hurt it in the end (we'll get to that later), even if Sternberg was right to stand by the exclusive distribution and high production value packed within each garment

In October of 2013, Band of Outsiders launched its first store in Tokyo after taking loans from numerous investors. Sternberg’s decision to open in Tokyo was based on the brand’s success with Japanese men, who already embraced Thom Browne’s similarly styled clothing. Soon after building the store in Japan, Sternberg took more investments—most notably from CLCC SA—and announced plans to build the Band of Outsiders flagship store in SoHo. The flagship store was finally opened in September of 2014 at an astonishing 5,000 square feet, featuring an in-house Momofuku Milk Bar. The store was subtly extravagant—a simultaneous ode to both the Los Angeles film fan and the SoHo shopper—a detail that applied to much of the brand’s clothing.

In May of 2015, a report emerged from Fashionista that Band of Outsiders had laid off more than half their staff, with plans to close the SoHo and Tokyo store. The costs of operating two stores in major cities as well as designing and producing full men’s and women’s lines each year became too high for the brand’s slim profit margin and minimal sales. Within a few years, the brand had racked up over 2.5 million dollars in debt. The in-store garments were sold quickly at heavy discounts, and the store was closed by June.

Soon after closing both stores, Sternberg sold the rest of his shares of Band of Outsiders to CLCC SA and vanished from his position at Band of Outsiders as well as the public eye. In July of 2015, CLCC SA held an auction to sell the rights to the brand as well as the remaining inventory for over two million USD, but there were no bidders. CLCC SA decided they would temporarily shut down the brand, with the hopes of re-opening the brand when they figured out how to make it profitable.

In April of 2016, CLCC SA announced that they were re-launching Band of Outsiders. Having already hired a new team, Band of Outsiders was set to showcase the Spring/Summer 2017 collection in September during New York Fashion Week. Under the lead of experienced Belgian designer trio Nick Hodel (Louis Vuitton), Matthias Weber (H&M), and Florian Feder (Dries Van Noten), Band of Outsiders was bound to be an eclectic mixture of styles. In an interview with Business of Fashion, Nick Hodel said, “It will be a re-launch. It won’t be a copy of something someone else created with his blood, sweat and tears. ” The European designers unveiled the first show, which seemingly had no connection to Sternberg’s brand, except a shared name. The trio promptly left after the first collection, leaving Band of Outsiders seemingly lost at sea for the second time in less than two years.

In November of 2016, after considering closing Band of Outsiders, CLCC SA hired Daniel Hettmann, a brand strategist, to lead the second Band of Outsiders re-launch, and Angelo Van Mol as the creative director. In an interview with GQ, Hettmann said, “I think the DNA of the brand is still the same, but this is just our own interpretation of that DNA.” He added, “The prints were always incredibly important and for this first season they're really, really graphic.”

While certainly similar to Sternberg’s Band of Outsiders, Hettmann’s Band of Outsiders is a more intelligently constructed brand. Since the brand primarily uses European fabrics and production, its main headquarters are located in London, significantly cutting the brand’s costs. While based out of the UK, Hettmann recognizes that Californian style is deep-rooted within the brand. Hettmann has regained some of the brand’s original American following, while also appealing to Europeans through combining British and Californian fashion. Hettmann also has expanded Band’s market through reducing retail costs (arguably the main issue plaguing Sternberg’s iteration) and making garments suited for people of many body types.

Nonetheless, Band of Outsiders is still, at its core, a Band of Outsiders. While they are not continuing Sternberg’s signature Polaroid campaign, the brand is utilizes the spirit of OG Band of Outsiders by centering around performers—this time tapping underground British comedians for their Spring/Summer 2018 presentation. Hettmann wants to continue the humor around the brand, saying, “it's all about not taking ourselves too seriously. I think that’s a bit too present in fashion right now. ”

It’s good that the current directors of Band of Outsiders have a sense of humor. So much turnover in such a short amount of time is sure to breed uncertainty about the direction of Band, no matter how successful the brand may become in the short term. But if there’s one thing that has remained across Band of Outsiders’ many iterations, it’s a constant push to fuse fashion, cinema and Californian charm—something Sternberg embedded into the brand from day one. Of course, it’s hard to say that the latest iteration of Band is the completely aligned with Sternberg’s original vision, but its resilience and...well, outsider attitude is an asset that’s carried over across Band of Outsiders’ selection of creative directors. Showcased in the pair’s latest collection, it’s clear Hettmann and Van Mol plan on using the brand’s now-enigmatic status to work outside the confines of traditional fashion dialogue. In that way, the brand has always been an Outsider in the fashion world.