From The Bros Who Brought Men’s Short Shorts Back In Style: Hawaiian Shirts

If Chubbies has its way, the Hawaiian shirts your dad wore in the ’80s are about to make a comeback.


You can thank Chubbies Shorts for all the men who bared their legs (and thighs) this summer.


Judging by the short shorts and gross mustaches men are sporting these days, ’80s fashion is making a comeback. At the forefront of this movement is San Francisco apparel company Chubbies Shorts. Since launching in 2012, the venture-backed startup has built a fanatical following among 18- to 35-year-old men–a coveted demo for marketers–with its irreverence for pants, office life, and The Man. As Chubbies embarks on a new chapter, it’s hoping to do for Hawaiian shirts what it did for short shorts.

Though the company does not disclose user numbers, across social networks it has amassed 1.4 million fans, close to a million of them on Facebook. What’s most remarkable is that Chubbies has managed to get men to open up about fashion and fuel the company’s marketing strategy by submitting photos–yes, including countless crotch shots–of different moments captured while wearing Chubbies’ funky above-the-knee shorts: while doing a keg stand, while hanging in the kiddie pool with the dog, or while catching a fish with one’s bare hands (NBD).

When the company raised $4 million in April, Rothenberg Ventures, a firm of largely millennial investors, was on board. “They have this exuberance for life and very inclusive joyful approach combined with an extreme work ethic and effective messaging based on listening to their customers,” says CEO Mike Rothenberg, who describes himself as a “long-time customer, friend, and now investor.”

The four Stanford buddies who founded Chubbies–Tom Montgomery, Rainer Castillo, Preston Rutherford, and Kyle Hency–draw inspiration from their dads in the ’80s. (The guys also admire Tom Selleck, whose portrait–billowing chest hair and all–graces a wall in the Chubbies office.) While looking at old photos, the founders noticed common elements: macho dudes, gnarly mustaches, short shorts, and Hawaiian shirts.

Check, check, check, and–then a light went off in their heads. Sure, these bros were united in their fervor against pants (even creating tuxedo shorts for unavoidably fancy occasions), but when the company looked to expand its offerings, Hawaiian shirts seemed like a natural fit. After about a year of development, Chubbies on Tuesday will open up preorders for a line of Aloha shirts, featuring vivid and wild patterns, called–wait for it–the Nutter. The shirts will retail for $74.50 and ship in November.

Rendering of pineapple-patterned Hawaiian shirt.Illustrations: courtesy of Chubbies

The founders say they created the Nutter out of necessity (as necessary as these can be, anyway). “If I look at the market today, Hawaiian-style shirts are too snug and for hipsters, or way too large and built for a 400-pound man,” Castillo, head of product and design, tells Fast Company. “I am by no means Adonis’s model of perfection. I’m a 250-pound man who has a pretty good beer belly.”

The Nutter is all about embracing men’s imperfections. “As opposed to companies like Abercrombie & Fitch [which, it’s worth pointing out, debuted a line of short shorts earlier this year], where you have shirtless models with six-packs and guns ablaze, ours is rooted in, ‘This is a man’s brand. These are real guys who are hairy and have bellies and like to go out on the weekend,'” says Montgomery, who oversees marketing, web design, and customer support.

Indeed, Chubbies is a brand that lives for the weekend. Continuing its campaign against work-appropriate attire, it’s now protesting the top button. To Chubbies, the top button symbolizes a drab life in a drab office. The lack of a top button, however, evokes “barbecue, grilling, and a dang good time,” says Montgomery. Instead of creating a button-down, Chubbies landed on a popover design in 12 different patterns, including pineapples, parrots, boats, and a variety of floral prints.

A Nutter shirt featuring toucans and macaws.Illustrations: courtesy of Chubbies

The company has been known to experiment with research and development, producing such innovations as reversible shorts (perfect for a quick barbecue costume change), shorts that reveal a pattern when exposed to water (neat party trick), and thick-fleeced Sherpa shorts (practical for zero occasions). But for its shirt launch, crazy patterns will have to do. “The real differentiator in these is around fit, pattern, wash, and real basics,” says Castillo. “We don’t want to make [the Hawaiian shirts too] flashy on day one, in addition to it being outrageously casual.”

But down the line, expect wild ideas, perhaps shirts with glow-in-the-dark patterns. “That same innovation will certainly apply to shirts as we get moving. It will be a fun time–whether or not people wear them is another story,” says Montgomery.

About the author

Based in San Francisco, Alice Truong is Fast Company's West Coast correspondent. She previously reported in Chicago, Washington D.C., New York and most recently Hong Kong, where she (left her heart and) worked as a reporter for the Wall Street Journal