How Short-Shorts Company Chubbies Is Tackling Winter Wear

You can now top your thigh-baring shorts with loud (but cozy) half-zip sweatshirts.

The Chubbies Man needs more clothing on the weekend.


Or at least, that’s the point Chubbies has slowly been trying to make since launching three years ago as an online purveyor of short shorts and Tom Selleck-era nostalgia. “We wanted to bring back what we saw as a critical item for our dads and people of the ’80s and ’90s,” says cofounder Rainer Castillo, head of product, manufacturing, and design. “But over time, we had this opportunity to morph from just a shorts company into something else.”

Along with cofounders Tom Montgomery, Preston Rutherford, and Kyle Hency, Castillo has been working on curating the perfect assortment of items for the Chubbies Man to wear on the weekends, which they’ve been trying to liberate from the tedium of weekday workplace attire with brightly colored and boldly patterned clothing. In 2012, they released their standard 5.5-inch short, with swim shorts debuting in 2013 and the Nutter—a Hawaiian-style shirt and the company’s first nonshort garment—following the year after that. This year’s new product, however, marks what might be a turning point for the e-commerce startup.

In what Castillo calls “a major departure,” Chubbies is announcing a line of sweatshirts called the Chubbies Half-Zip, the apparel company’s first foray into outerwear. Whereas earlier offerings have been decidedly friendlier to summer weather thanks to shorter hemlines and top-button-free shirts, the half-zip introduces the brand’s target demo of 18- to 35-year-old men to attire for the other half of the year. The sweatshirts will be available to order online for $79.50 and will ship immediately while supplies last.

Though it’s taken three years for Chubbies to introduce the half-zip, Castillo says it has been at the back of their minds since day one as the perfect third piece to round out the Chubbies Man’s wardrobe. “As a brand, we’re here to build all his essential needs for the weekend,” he says. “Any time you’re going away for a three-day weekend, or if you’re walking home from work one day, this should be something you throw in your bag.”

Castillo, who had his whole team bring in their favorite sweatshirts as an exercise in deciding what to create, hopes the half-zip offers the same emotional connection to the past as previous pieces do. Their inspiration came from wanting to tap into the nostalgia behind the worn-in, washed-out garment most people think of when picturing their favorite sweatshirt. “No one actually thinks of something they bought last season,” says Alexis Boeriu, director of new product development. “They want something that makes them feel great and at home when they wear it.”

Development lasted a year, about as long as most products take at Chubbies, which prides itself in thoughtful but quick turnaround, thanks to a domestic supply chain that includes 600 sewers across factories in California, Arizona, and Texas. The biggest challenge was finding a source that could actually make the ideal fabric: something heavy enough so that a guy could wear shorts in the winter along with the half-zip, but also rugged enough that it could last years of wear. Once they found a mill in North Carolina that was up to the job, Boeriu says it was only a matter of leveraging their existing base of vendors to create a product they could all be proud of.


The half-zip will come in six designs, each one retro-inspired and, unlike the heather gray crewnecks Castillo says everyone is making, unafraid to be bold. “These embody the spirit of our customer and what he’s already wearing,” he says. “He’s typically a loud guy; he likes to stand out.”

The company will likely tweak the half-zip in the coming months, taking the same inventive approach with those future iterations as they have with their shorts (think Sherpa-lined shorts and tear-away swim trunks). And while they are adamant about never creating pants, Castillo says the next 12 to 24 months may finally see their first product for women, who, despite accounting for 20% of Chubbies’ audience, have never had a product on the site outside of a limited collection of patriotic-themed shorts.

For now, the half-zip represents the brand’s latest move to invite everyone into its community, which includes almost 300 college ambassadors and 2.5 million fans across social networks. And while future products, especially a women’s line, will likely require more intensive planning going forward, Chubbies aims to take slow but certain steps towards becoming the go-to brand for the weekend.

“We’re pointing the whole ship in a broader direction,” says Castillo. “We always want to give them something they can’t get from someone else.”