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Chicago Startup Mugsy Jeans Is Helping Guys Find Stylish Jeans That Are Actually Comfortable


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Image via Mugsy Jeans

In a hyper-competitive denim market that's dominated by legacy name-brands like Levi Strauss, Wrangler, Lee and a host of others, it can be challenging for upstart jean companies to find room in consumers' closets.

But Chicago startup Mugsy Jeans appears to have broken through the denim noise with a jeans brand that's resonating with customers. Its annual revenue is in the seven figures, according to founder Leo Tropeano, and the startup hasn't taken a drop of venture capital.

Founded in 2015, Mugsy set out to create a stylish jean for guys that didn't compromise on comfort and durability. It got some flashy press from outlets like ESPN and Esquire, who noted how Mugsy looked good on hockey players who have thick quads and glutes, as well as guys who are, um, large in other areas.

But really, Mugsy Jeans are for any guy who feels skinny jeans are too constricting and baggy jeans aren't fashionable enough, Tropeano said.

"To look good I have to be this uncomfortable?" Tropeano said, describing his experience trying on high-end jeans. "That didn't seem right to me. How is there not a better answer?"

Tropeano went to work creating a proprietary denim blend that was flexible, durable, stylish and retained its shape after multiple wears. Sourcing denim from a factory in Asia, Mugsy began selling online in 2016 and is growing revenue 3-4X per year, Tropeano said, noting annual revenue is in the "millions."

Mugsy is also profitable, Tropeano said, a notable accomplishment for a young denim brand operating in a competitive, cash-intensive industry.

"We've been really good at being efficient with our capital," he said.

Mugsy has less than 10 employees at its Fulton Market headquarters. Its jeans costs less than $100, and it also offers chinos, shorts and swimwear. The startup sells nearly all of its clothes online, except for its appointment-only showroom at its Chicago office.

The startup has done limited advertising outside of podcasts, where it has run spots on the popular Pardon My Take podcast and other Barstool Sports shows. Tropeano also said the company has a deal in place to advertise on the Howard Stern show later this year.

Mugsy faces a handful of VC-backed competitors, like Los Angeles-based DSTLD and San Francisco-based Everlane. In Chicago, Zipfit Denim has developed proprietary technology to help people find the best-fitting jeans, and it's raised $2.2 million from investors such as Irish Angels and M25.


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