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The House of Boomshakalaka

Ellen Cushing | July 4, 2014 | Story Fashion

The offices of San Francisco's hottest fashion startup look distressingly like Omega Theta Pi. Though the online-only men’s shorts company Chubbies is rich with venture funding (and, in typical techie fashion, employs a private chef to drop off hotel pans of hot lunch and plates of fresh-baked cookies daily), the vibe at its Potrero Hill headquarters is decidedly less startup sleek than frat-house maximalist. A big-screen TV planted in front of a leather couch silently plays reruns of Two and a Half Men to an audience of no one, and posters with slogans like “Sky’s Out, Thighs Out” parrot the company ethos back to its employees.

The place is littered with theme-party tchotchkes: A half-deflated beach ball sits dolefully in one corner; a comically oversize sombrero hangs from a coatrack; a truly massive American flag covers one wall. In the basement room that served as the center of manufacturing before the company got too big and moved some of its operations to L.A., a foosball table sits dustless and proud among piles of loudly colored fabrics. In the conference room–cum–intern den, a white-board is emblazoned with the mantra “Scalable Synergistic Solutions”—a joke, the guys hastily point out, put up in the service of one of the brand’s many YouTube videos. (In the ironically low-budget 50-second clip, a horizontally split screen shows a man’s business-casual top half engaging in clichĂ© workplace drudgery as his legs, wearing Chubbies in a garish ’80s print, jerk spasmodically to the sounds of “U Can’t Touch This.”)

Like at many startups, the line between Chubbies’ customers and its employees is unrecognizably blurry, which means that everyone in the office—men and women, C-level execs and interns—wears Chubbies’ one and only product: a cotton short that’s cut to the mid-thigh and comes in more than 70 prints and colors. Even the accountants, the only people here who appear to be over 30, wear Chubbies, albeit with pressed oxford shirts. Sitting in the aforementioned conference room, the company’s founders say that they haven’t worn long pants in years. They say it very proudly.

“It’s like, once you start wearing Chubbies, you never want to go back to long pants,” says Rainer Castillo, one of the company’s four founding fathers. He beams as he relates a story about going to New York earlier this year to meet with investors and reporters, all of whom were shocked to see his bare legs in the below-freezing weather. (When Castillo’s cofounder Kyle Hency got married last month, his fiancĂ©e insisted that he wear a suit for the ceremony—but Hency stood firm on changing into Chubbies for the reception.)

Castillo, Hency, and their cofounders, Preston Rutherford and Tom Montgomery—all friends dating back to their days at Stanford in the mid-aughts—created Chubbies on a lark after a Fourth of July trip to Tahoe: They had made a small batch of American flag–print shorts in a ’70s-style high cut to wear as part of an annual “ultra-patriotic” costume party, selling the extras to friends to defray costs. People liked the skimpy designs so much that the buddies kept making them. Soon enough, Castillo says, “it became sort of obvious for us.” Castillo had years of experience in corporate retail, first at Gap and then at Levi’s; his cofounders were working in customer service, venture capital, and software, all integral to a venture-funded e-commerce site. They put their savings into a company, and soon enough, Chubbies—named for the shorts’ elastic waistband and also for boners—was born. “From fun to business happened really softly,” says Castillo.

Crucial to the early success of Chubbies was its college ambassadors program, in which members of the brand’s target demographic—that is, fraternity presidents—are recruited to spread the gospel on campuses across America. When the newly incorporated company officially unveiled its first line of shorts—made of brightly colored, heavy-duty cotton, with “Boomshakalaka,” a favored interjection, sewn behind the zipper—in its web store in March 2012, it sold out almost immediately. For the rest of that year, the founders couldn’t manage to keep their product on (virtual) shelves, despite ramping up their production run by orders of magnitude and contracting out the sewing. By the end of 2012, 18 months after that fateful Tahoe weekend, they’d hired eight more staffers. As of this spring, the company had 30 employees, and it has added manufacturing operations in Oakland and L.A. (Chubbies are, in company parlance, “made in the good ol’ U.S. of A.,” which is increasingly rare in mass-market apparel.) Though the Chubsters, as they call themselves—the company has no one CEO or CFO, just the self-styled “quadfecta of management excellence”—are cagey about numbers, they will allow that 2013’s sales were more than triple those of 2012. Sales can top 10,000 pairs on a really good day; with each one going for $50 to $60, that’s half a million dollars in revenue. According to Castillo, if the company isn’t yet the largest domestic manufacturer of men’s shorts, it’s on track to be soon. Men’s shorts is a $3 billion industry with no clear leader, and the Chubsters are nothing if not confident.

Like so many other startup founders, the men of Chubbies talk about their product with an almost evangelical fervor. In their view, the relatively short 5.5-inch inseam is about “liberation,” the company is in pursuit of nothing less than “revolution,” and the reactions of fans are “visceral.” The half-ironic “Chubbies Facts” that lard the company website speak to both Chubbies’ higher purpose and its broheim aesthetic, a nostalgic, fiercely hetero kind of masculinity. #23: “You will be sheltered from the cold by a thick layer of sweltering women latched to your radtacular man thighs like a pack of starving koala bears.” #26: “If you wear shorts longer than Chubbies, you probably don’t love America.” #32: “Cargo shorts are the only form of contraception that is 100-percent effective.”

Rutherford elaborates. “The Chubbies guy is a great guy,” he says. “His thighs are completely liberated. He’s wonderful to his mother and his sister. He picks on his little brother a little bit. He drinks Budweiser at the bar. If his buddies roll in, he’s the guy to get the first round.” He loves his bros, but you know, not in a gay way. He really loves his dad. He loves the weekend—like, a lot. He loves America, and grilling, and beer. More specifically, judging by a highly nonscientific poll of the crowd at Chubfest—the company’s first foray into large-scale brand activation, a massive, ’80s-themed party at Slim’s in March—he is white, under 30, works in finance or tech, and finds liberation not just in his inseam but in the safe hedonism of drinking games and cookouts that Chubbies represents. Nationwide, the company is most popular with college-age men, particularly in the South, where its patriotic, ultra-manly message (and a shorts-friendly climate) resonates the most.

“We wanted to bring to mind the anti–male model,” says Montgomery, straightening himself in his chair as his vision reveals itself. “We wanted to convey a man’s brand. It’s like, you’re walking down the streets of New York, and you see on the right side an Abercrombie & Fitch store with a guy with six-pack abs and his shirt off and he’s spraying cologne, and you smell him from two miles away. And on the left side of the street, Chubbies has barbecue scent a mile down the road, with a couple of big hairy dudes in their shorts grilling and inviting you to come have ribs or whatever, and have a party and not worry about it too much. That is kinda the juxtaposition. We want to create this club where guys can live the weekend lifestyle every day, all the time.”

It’s working. Chubbies’ college ambassador program now receives thousands of applications a year, and the company has a vast and active online community, with nearly three-quarters of a million fans on Facebook alone. In April, it received its first round of venture funding, $4.5 million from investors including Chris Burch, cofounder of the women’s fashion empire Tory Burch; Blair Lambert, a former executive at Gymboree; and Brian Spaly of the men’s clothing startup Trunk Club.

“Ultimately, we want people to think of us emotionally,” says Castillo, “where when they think about us, they think about fun, and the lightheartedness that we’re trying to put into everything. The brands that we look up to are brands that have established a really, really amazing emotional connection with their customers.” That means not necessarily J.Crew or the detested Abercrombie & Fitch, but companies like Nasty Gal, Red Bull, and Tommy Bahama—corporations that have successfully turned themselves into a lifestyle by cannily marketing to a consumer base that’s more than happy to define itself by its taste.

But allying a company so closely with a very specific lifestyle is a double-edged sword— after all, the company’s founders have lived in the Bay Area long enough to know that frat culture turns off as many people as it excites. And they themselves are wary about using the B-word: “bro.” “We get really sort of nervous about that label because we think we’re very inviting to everyone,” says Castillo. “At no point are we ever going to be saying, ‘You guys shouldn’t wear our stuff.’”

It’s a smart strategy—exclusivity is, after all, a bad business practice. And though the Chubsters may be happy to wear shorts year-round and may work in an office where they’re not just allowed but required, not everyone else is and does. College kids graduate and get desk jobs. Winter comes. The weekend ends. So the quadfecta of management excellence is tentatively wading into other ventures—a line of swim trunks is doing well, Chubfest was a huge success, and the guys half joke about creating a line of beer koozies and snug ’70s-style T-shirts. “As we think about it, Chubbies very organically becomes the lifestyle brand for a guy with a full wardrobe and a full set of weekend opportunities,” says Rutherford. “We’re walking into it cautiously, but we think we have a cool way to grow.” Sounds like a scalable synergistic solution.

Originally published in the July issue of San Francisco

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