How Chubbies is Conquering the Men’s Shorts Business on Shopify Plus

How Chubbies is Conquering the Men’s Shorts Business on Shopify Plus

Life has been one long weekend for Tom Montgomery.

Unfortunately, the co-founder of vintage shorts retailer Chubbies fears the weekend is in danger as the work week for many has ballooned to 60, 70, or even 80-hours. As longer work weeks become more common, Montgomery believes the weekend is something which deserves to be fought for and reclaimed.

“The weekend has definitely become endangered,” Montgomery bemoans. “Are there bigger problems on Earth, absolutely, but it really bothers me that people are constantly frustrated and stressed, and not taking time to relax and care for themselves.”

What’s to blame for the death of the weekend?

Shorts that lead to “unliberated thighs,” according to Montgomery.

He’s only partially kidding…

The Cargo Curse

Montgomery and his buddies grew up in an era when the world of fashion was ruled by male models with washboard abdominals who would spray funky-smelling cologne on you as you passed by their storefronts.

“The shorts de jour were cargo,” Montgomery recalls. “These things weren’t custom designed for anything; they’re moderately cooler but almost as long as pants which makes no sense for a man looking to be cool and comfortable.”

The idea of conformity and an undifferentiated one-size-fits-all mentality not only makes for poor fashion Montgomery suggests, but also indirectly contributes to the erosion of the weekend and what it should symbolize for American men.

To restore some of the individuality that makes weekends special, Montgomery knew he wanted to flip the world of men’s fashion, specifically men’s shorts, on its head.

But it wasn’t immediately clear how this would happen.

At least it wasn’t until Montgomery and three friends inherited something that would change their lives.

And maybe yours…

The Heavenly Hand-Me-Downs

Montgomery and three friends from Stanford University- Rainer Castillo, Kyle Hency, & Preston Rutherford- were well on their way after graduation to promising careers in traditional businesses like venture capital, finance, and retail.

But they were “working for the man” and they didn’t love the man.

Back in their college days the four were known for wearing short shorts; the kind of thigh-liberating pieces you might see on NBA legends like Larry Bird:

Image via: Sports Illustrated

“These shorts were magical, just incredible,” Montgomery recalls fondly. “They were passed down to us by our dads and uncles and they were amazing because these shorts were how we defined our weekends.”

In 2011, several years after graduating, Montgomery and friends planned a Fourth of July trip to Lake Tahoe. As always, the group planned to wear vintage shorts but this time, after pooling their money, they had 25 extra pairs made to take along.

The four had always wanted to start a business and decided to use the weekend as a test. The extra shorts were jammed into backpacks and Montgomery and team hit the beach wearing the thigh-revealing shorts they had a hunch might sell.

“We saw an intense reaction,” Montgomery remembers. “We sold out quickly and afterward people were offering to trade their shorts for the ones we were wearing.”

Proof of concept…


The Rebirth of the 5.5’ Inseam

The team of vintage shorts hawkers weren’t actually selling shorts.

Rather, the founders of Chubbies wanted to sell the weekends of yesteryear; the ones they grew up loving as children and the ones they want to help others reclaim. The Friday at 5 o’clock crowd itching to let go of the week’s stressors are the very people for whom Chubbies was created.

“We wanted to sell our lifestyle to people,” Montgomery said. “When we decided to start this business we wanted to sell the notion of fun and embody that in every pair of shorts we sold.”

So Montgomery and his buddies quit their jobs and set out to upend a slice of the fashion industry while simultaneously helping men reclaim their dying weekends.

Hence, the birth of Chubbies and the rebirth of the 5.5-inch inseam.

The Shorts-Breathing Dragon

The initial run of shorts that sold out that Fourth of July weekend proved to Montgomery vintage shorts resonated with others who were reminded of their dads and the fun had on weekends. So Montgomery quickly built a website to market another handful of shorts.

The result; another rapid sell out.

The scenario repeated itself several times.

The early success was great and would eventually lead to several rounds of venture capital funding but Montgomery and his friends wanted to create something different:

  • A different type of product
  • A different way of marketing it
  • A different way of manufacturing it

“We’re just a small company doing big things,” Montgomery says. “The story we’re telling is big, emotional, and it’s our dream and we began seeing our customers are just as passionate about these things as we are.”

The Product

Retro-inspired shorts are polarizing.

There were some at that lake Tahoe beach who thought men’s legs were something that ought to be covered, not shown off.

But the American flag-like original run of shorts would become a cornerstone for the brand.

Image via: Chubbies

The American dream the Chubbies founders are living is possible, in part, because of the sacrifices made by our armed service members. Castillo’s father served as did both of Montgomery’s grandfathers.

“We want our products to recognize these guys,” Montgomery said. “The fact is what they do has allowed us to create a shorts company which is absolutely amazing when you think about it.”

Service members around the world have noticed and are responding by dropping their fatigues to reveal shorts Montgomery hopes provide a moment of levity or comfort in otherwise stressful or dangerous environments.

Image via: Chubbies

The only ecommerce home the Chubbies brand has ever had has been on Shopify and now Shopify Plus, an enterprise ecommerce platform for high volume merchants. “We’ve been with Shopify from day one,” Montgomery boasts. “None of us are engineers so it’s great to be able to rely on Shopify’s experts so we can focus on innovating.”


We’ve been with Shopify from day one.


Besides crediting Shopify with enabling Chubbies to easily offer military discounts, Montgomery says not having to worry about IT is something that helps differentiate the company.

It’s why we are a different company,” Montgomery says. “The platform is easy and fast and frees us to create content that’s building our brand.

The Marketing

You won’t often see Chubbies advertising like its competitors with big banner ads or those annoying full screen pop-up interstitials.

“We have a mindset of let’s earn their attention and trust,” Montgomery says. “We create a lot of content but the rule is we have to give them something they enjoy or we’re simply not going to do it.”

The way Chubbies talks about shorts is fun, ridiculous, and edgy. For instance, the company’s manifesto reads, “To us, pants are a necessary evil- built for the work week because your boss doesn’t get it.”

Image via: Chubbies

Rather than talking at their customers, Chubbies tell stories with their customers as evidenced by volumes of user generated content illustrating the Chubbies’ lifestyle:

Image via: Chubbies

To become a global ecommerce brand that defines the weekend and one to which everyone can relate, Chubbies recruited college campus ambassadors to spread the word. The way Chubbies puts it, ambassadors are its, “Badass crew of thigh-liberating patriots you’ve been hearing so much about.”

Image via: Chubbies

Instead of interrupting prospects with special offers, sales, or “buy now” calls to action like the majority of retailers, Chubbies opts to let ambassadors and customers tell the brand’s story visually and in ways prospects can internalize.

For example, you know Montgomery hates cargo shorts. But rather than endlessly rail against them itself, Chubbies lets customers do the talking- or showing:

Image via: Chubbies

“Our marketing is totally different because we’re about giving people awesome experiences,” Montgomery says. “It’s all about having the best content and ours is better, faster, and crazier than the competition.”

But there’s more to being different than frat parties and fun.

The Manufacturing

“We are hyper competitive,” Montgomery says. “Anything that gets in our way is something we have to go around or over.”

One of those hurdles, manufacturing apparel, is the third way Chubbies differentiates itself from the competition.

Chubbies charges a premium for its shorts, between fifty and sixty-five dollars a pair, but customers appear happy to pay, in part, because the shorts are sourced and manufactured in the United States. At first blush, you might think this puts Chubbies at a competitive disadvantage to companies with less expensive overseas manufacturing. But Montgomery says making shorts in the U.S. is consistent with the Chubbies’ brand.

“It takes a strong commitment to manufacture here,” Montgomery says. “Our customers understand it’s a bit more expensive but that’s because we’re investing in the U.S. and creating jobs our competitors outsource.”

The Chubbies supply chain has become a valuable asset. Not only does building out that chain in the U.S. put Chubbies closer to its suppliers which enables quicker product turns, but piecing together the chain over the last four years creates a competitive advantage difficult for larger competitors to mimic.

“There isn’t a one-stop-shop for manufacturing apparel in the U.S.,” Montgomery says. “While a minor problem in a chain we piece together can cause delays and other issues, there’s a ton of expertise in the U.S. and our customers reward us for putting our faith in the U.S. worker.”

Chubbies sources cotton from mills in North and South Carolina. Afterward, it’s dyed and sewn in several manufacturing facilities in California, where Chubbies is headquartered. It’s an example Chubbies hopes competitors will follow even if it erodes the advantage Chubbies has created.

“We want to teach our competitors it’s possible to manufacture here,” Montgomery says. “As competitive as we are, if we could get competitors to follow our lead we’d love to be part of spearheading that.”

If Chubbies gets its way, it may soon have the brightest spotlight of them all highlighting the differences that make it unique.

The Chubbies Bowl

“We’re a scrappy little company,” Montgomery says of his 35-person team. “We pull together and emphasize doing more with less and that earns respect money can’t buy.”

That ethos has earned Chubbies plenty of attention and may just earn it 100x more.

Today, more than 1.5 million people are part of the Chubnation, otherwise known as the dedicated group subscribed to receive content from Chubbies. But the Chubnation could grow exponentially if the company wins the equivalent of a multimillion dollar marketing opportunity of a lifetime; a free Super Bowl commercial.

“The exposure would be unreal,” Montgomery says. “We are super amped about the opportunity and would be hyper grateful if people would help make it happen.”

Chubbies recently entered the Quickbooks Small Business Big Game competition for a chance to win a free Super Bowl commercial. More than 15,000 businesses entered the contest and Chubbies was selected as one of ten finalists. The winner, which will be determined by the company that gets the most votes, will be announced in November.

Image via: Chubbies

Super Bowl commercials are generally reserved for big brands with deep pockets and cost nearly $5 million last year. An audience this size, more than 114-million people watched last year, would undoubtedly help Chubbies grow faster than its current clip of 50% year over year.

“If we win this I promise you’ll see a first-of-its kind type of commercial,” Montgomery teases. “We have huge imaginations here and a Super Bowl commercial would allow us to be ridiculous, crazy, and educate people about American manufacturing all at the same time.”

The timing couldn’t be better.

Just as it’s vying for a Super Bowl ad, Chubbies is also set to launch its first ever worldwide male model search.


Rather than pictures of the founders in skimpy shorts or professional models with rock star-like features, Chubbies wants real men to show off their retro shorts known for their forgiving elastic waist bands.

“We are stoked to find relatable guys to do fun stuff with,” Montgomery says. “We’re gonna open the casting call to every regular guy on earth, help them make really cool content, and feature them in ads and billboards.”

And who knows, the regular guy models selected just might work their way into supporting roles in the Super Bowl ad should Chubbies pull enough votes. To smooth out the seasonality of selling shorts, Chubbies has expanded and now offers shirts and will soon offer what the company calls jacket shorts, or shorts you put over your vintage shorts to keep you a bit warmer so you can wear Chubbies year-round.

“It would be insane,” Montgomery says as he laughs thinking about the number of new customers a Super Bowl ad might wrangle. “It’s crazy, exciting, risky, and scary but we’d ramp up quickly and are asking people to help a small business that’s in this for all the right reasons.”

So what’s in it for you?

If Chubbies wins the contest, it’s inviting each and every one of its customers to its San Francisco headquarters for a Super Bowl commercial viewing party guaranteed to provide everyone a stroll down memory lane to a bygone era that, win or lose, Chubbies is trying to bring back for good.

By the way, that Super Bowl ad would air in the dead of winter.

But you can bet everyone at the party will be wearing shorts.

Vote for Chubbies here.

About the author

Aaron Orendorff

Previously the Editor in Chief of Shopify Plus, Aaron Orendorff is the VP of Marketing at Common Thread Collective. Named by Forbes as one of the top 10 B2B content marketers, his work has appeared on Mashable, Entrepreneur, Business Insider, Fast Company, Inc., Success Magazine, The Next Web, Content Marketing Institute, and more.

Check out Aaron Orendorff’s work