To: Kyle Hency, Co-Founder of Chubbies

Dear Kyle,

Chubbies has, from the beginning, been all about the weekend. This focus has powered the brand’s success to date, creating a thriving cadre of men (and some women) who have strong and positive feelings about a company that makes short shorts.

But as you look toward your next chapter of growth, a opportunity lingers: the other five days of the week. While many people would probably like to wear Chubbies products to work during the week, most are barred from doing so for a number of reasons. But as the workplace grows increasingly casual, Chubbies has an opportunity to expand its assortment for every day of the week.

Here’s one idea about how to do it:

Launch Chubbies Undercover.

Chubbies products and customers might be best represented by the saying “loud and proud.” This approach has made an enemy out of pants, button downs and other formal attire—necessities of working life.

But what if you embraced the enemy? Chubbies could launch a line of pants, button downs and maybe even suits and ties that look rather normal on the outside, without sacrificing the brand’s style and mentality: Each piece could include a few Chubbies accents and be full-stop Chubbies on the inside. The chinos could have a stripe on the side, a special cuff on the bottom, or bold belt loops, with an inside lining that is 100% “loud and proud” Chubbies patterns. The button downs could have special buttons, collars or cuffs, with unfiltered Chubbies bleed on the inside. The same concept could work for suits, ties and other workplace staples.

To push the idea even further, you could make these products fully reversible—a true manifestation of the day-to-night outfit, allowing your customers to seamlessly transfer from work to play, weekday to weekend, the second that Friday at 5pm hits. Maybe those cargo zip-offs were on to something.

This would be an exciting new feature for the brand, driving lifetime value for existing customers and opening up the brand to a whole new group of customers who couldn’t rationalize a purchase beforehand because of their business professional or business casual fashion restraints. This approach would work especially well for womens’ styles, which would allow you to broaden your product offering and customer base beyond men’s.

Naysayers might call Chubbies Undercover dilutive to the overall brand, but if executed correctly, the initiative would be entirely additive to your brand. With much of your marketing and branding shunning or poking fun at workplace rigidity, Undercover gives Chubbies an extra edge—uniting utility with style, the workplace-friendly apparel would allow you and your customers to embark on a secret mission, building brand loyalty as you infiltrate the office.

This is one idea among many that would open Chubbies up to an ever-increasing audience while maintaining the resonance that made the brand successful in the first place. Let me know if you would like to hear more.

Richie Siegel
Founder and CEO
Loose Threads