How Chubbies Found Booming E-Commerce Success (and Where They’re at Today)

Gone are the days of the ‘90s and 2000s when nine-, eleven- and thirteen-inch inseams were en vogue. Very few men walk around with their shorts below their knees anymore.

That “fashion” movement came in response to decades of short shorts. When shorts became an important part of popular culture in the 20th century, they were a rebellion against long pants, and they swung towards the shorter direction — inseams below seven inches, often.

By the mid-2000s, short shorts were mostly reserved for athletics where longer shorts would get in the way, like running. Even basketball players leaned towards long shorts, though it was what men wore.

These days, everything has changed. Young men have completely rejected long shorts, shorts that extend beyond the knees and tickle their calves. What’s “in” now is short shorts once again, and it wouldn’t be a stretch at all to say that Chubbies is behind it.

Foundations: ‘Capital-F-Fashion’

In 2011, Kyle Hency, Rainer Castillo, Preston Rutherford, and Tom Montgomery started a business named Chubbies. The four had graduated from Stanford together a few years before, and their individual career paths weren’t satisfying them.

In college, they disliked the direction that men’s shorts were heading, so they went and found their own “retro” short shorts — at thrift stores. There had to be a better option for their short shorts, which always drew compliments — they set out to create it themselves.

The four friends were “repelled” by the traditional picture of men’s fashion, and decided to found a company that swam upstream. “The traditional world of men’s capital-F-’Fashion’ [was] completely unrelatable” to the young men trying to find their own way, and Chubbies was born.

Chubbies Takes On the Shorts Market

The founders tested their product wearing Chubbies to a Fourth of July function, and were blown away by how many of their friends loved the idea and the design. They brought a handful of samples for anyone who was interested — and sold out immediately. This confirmed their decision to leave behind their nine-to-five jobs, and they pursued the opportunity with fervor.

Chubbies was the four men’s “irreverent and visceral response” to their perceived downturn in modern men’s fashion, but it’s clear that their customers have always seen it in a more positive light. After the company launched in September 2011, it sold out of its main product, the casual short, for two consecutive years.

The shorts look (and feel) fantastic. Whether the occasion is a nice dinner, a pool party, or a day on the links, the Chubbies casual shorts can serve any purpose. Made with soft, stretchy material that also wicks water, their shorts are supremely comfortable and useful.

They do come at a high price point, however. A pair of casual stretch shorts will run you just under sixty dollars. This may turn some customers away, but Chubbies feels that the product is worth it; it’s built to last.

Reasons for Success

Without a quality product, no company can get off the ground. Fortunately for Chubbies, when their product was released, it was head and shoulders above any competition. For several years, Chubbies had a near monopoly on short-short e-commerce, and that’s how their start was so fast.

However, two years is a very long time to be sold out of a flagship product. The people loved the shorts, and they passed that information back to the company. With thousands of five-star reviews, even as competitors pop up left and right, Chubbies has remained a dominant force in the market

Every order over $35 ships free. Free exchanges are guaranteed for 90 days, and free returns for 30. The company also emphasizes giving back, with every purchase benefitting Foundation 43, an organization named for the 43 facial muscles that express emotion that is “on a mission to expand access to effective mental health care and suicide prevention in historically marginalized communities.”

Moving Forward

As Chubbies has grown and expanded, its product offerings have as well. What began as a simple design of a pair of shorts has grown to a massive apparel brand. The company offers dozens of different types of shorts in innumerable color schemes, in three different inseam lengths ranging from four inches to seven. 

They’ve also expanded to tops, offering long- and short-sleeve shirts along with flannels, graphic tee shirts, polos and tank tops. For $99.50, you can even purchase a set of Chubbies lederhosen with six-inch inseams. With 52 reviews averaging 4.9 stars on their Oktoberfest special, it’s clear that Chubbies is still focused on putting out excellent quality clothing.

Their newest full-time offering is a full-length pant, the first in the Chubbies lineup. Made with the same process and fabric as their classic shorts and marketed as the same Chubbies but cut full-length, the Everywear pant ushers in a new era for the apparel giant.

These days, it’s hard to go anywhere without seeing someone in Chubbies clothing, and it’s hard to blame their patrons. Their product is high-quality, they provide excellent customer service, and their offerings are expansive beyond belief. Chubbies his the jackpot when they brought back the retro shorts, and there’s no indication that their dominance is going anywhere anytime soon.