As Charlie Hustle’s new owners work to scale the Kansas City-built apparel company, the brand won’t lose its heart, they said, pledging instead to pattern expansion efforts after the vintage-feel and hometown-first ethos that made Charlie Hustle a go-to source for KC pride.
A critical piece of the plan: Hit new markets, city by city — Denver among one of the first — using local collaborators to ensure each market feels earned rather than generic.
“We don’t want to expand too fast,” said Matt Gary, co-owner of Charlie Hustle alongside his brother, Michael Gary, noting the importance of meeting demand without sacrificing quality or customer trust.
That restraint reflects a broader philosophy about the apparel market itself, Gary said. While barriers to entry have fallen — anyone can sell a shirt online — the brothers argue that long-term winners will be defined by quality, storytelling, and authenticity.
“There is an opening in the marketplace for high-quality products with deep stories — not just production art flips,” he said.
The Garys acquired Charlie Hustle in April 2025, now serving as co-presidents of the company popularized by founder Chase McAnulty after its KC Heart serendipitously hit the national spotlight in 2014. Financial details of the deal were not released.
McAnulty declined to comment for this story.
A key behind-the-scenes detail from the acquisition: The Charlie Hustle brand will now operate inside the Garys’ local-to-international apparel licensing platform, which includes Outdoor Custom Sportswear and Triform Custom Apparel. OCS has an exclusive license for Columbia Sportswear; Triform has a license for Adidas.
While the ownership structure is complex, the Garys said, their pitch to longtime fans of the brand is simple: The Charlie Hustle they love isn’t being rewritten — it’s being reinforced.
“We’re keeping Charlie Hustle the same,” Gary said. “The fun thing too is it’s also still owned by a local family — that’s very important. It’s coming from a local Kansas City family and going to another local family of Kansas City that really appreciates the brand.”
Joey Mendez at Charlie Hustle’s flagship store on the Country Club Plaza; photo by Haines Eason
Another point of reassurance, he said: Charlie Hustle’s flagship store remains in the heart of Kansas City’s Country Club Plaza — now with a familiar face behind the counter.
Relaunched at 419 W. 47th St. after lengthy renovations, the space is helmed by retail veteran Joey Mendez, the co-founder of ULAH, a longtime Charlie Hustle fan, and connection of both Gary and McAnulty.
From boutique favorite to platform fit
The Gary brothers see Charlie Hustle — named Small Business of the Year in 2021 by the Greater Kansas City Chamber of Commerce under McAnulty’s leadership — as a boutique endeavor with an intentionally different feel than their family’s other businesses, Gary said, and that intimacy is an essential asset.
In fact, Charlie Hustle’s loyal, regional following actually made the brand exceptionally attractive as an acquisition target to the Garys because the honest, plainspeak nature of the brand is nearly impossible to create out of whole cloth, he said.
So rather than forcing Charlie Hustle to conform to a corporate mold, Gary described the strategy as placing the brand “on top of our platform,” leveraging existing infrastructure — warehousing, decoration, logistics and a national sales force — while leaving the creative soul intact.
That platform includes Kansas City-based operations (although Charlie Hustle has moved out of its longtime East Crossroads HQ) with exclusive licensing relationships for some of the biggest names in sports and lifestyle apparel — a little-known reality that positions the region as a quiet powerhouse in the branded merchandise world.
“All of the five big apparel players, all of their collegiate merch is based out of Kansas City,” Gary said, pointing to legacy ties that trace back to his father’s first apparel licensing foray, Gear for Sports, and the city’s central role in logistics and distribution.
In other words, Charlie Hustle isn’t leaving Kansas City’s apparel ecosystem — it’s moving deeper into it.
Lettermen jackets line a stockroom shelf at Charlie Hustle. The brand plans to expand its products lines to include more polos, quarter-zips and performance pieces; photo by Haines Eason
Vintage-fresh remains the rule
Gary is empathetic with fans who worry that scaling Charlie Hustle will sand off the brand’s edges, he said, noting their strategy keeps Charlie Hustle rooted in its “vintage made fresh” ethos — from graphic style to fabric feel to the stories behind each design.
That includes the products that built its reputation: the soft hoodies, the well-worn tees and designs that feel both nostalgic and civic-minded. Expansion, Gary said, doesn’t mean dilution — it means breadth.
Under the new ownership, Charlie Hustle is expected to gradually add adjacent products like polos, quarter-zips and performance pieces, using the same materials and design sensibilities that customers already trust.
Just as important, Gary said, is maintaining the brand’s discipline around storytelling — resisting the temptation to “just sling ink” in favor of designs that actually mean something.
Enter House of Hustle
That belief in story-first expansion helped usher in the launch of House of Hustle, a new sub-brand designed to live alongside — not over — Charlie Hustle.
Chloe Elise, Deeper Than Money; courtesy photo
House of Hustle broadens the product mix while serving as a home for collaborations with entrepreneurs, creators, athletes and business leaders whose personal stories align with the brand’s values.
One of the first collaborators: Kansas City-based financial educator and Deeper Than Money founder Chloe Elise, whose own journey — from corporate employee to entrepreneur — mirrors the brand’s emphasis on perseverance and purpose.
“I’ve always leaned into the idea of hustle,” Elise said, framing the concept less as burnout culture and more as commitment to long-term goals.
Click here to explore the ongoing House of Hustle campaign.
For Elise, the partnership — first announced in November — resonated precisely because it didn’t feel transactional. She described Charlie Hustle as one of the first brands that made Kansas City feel tangible when she moved to the city in 2019 — a sentiment she already shared with her audience before any collaboration existed.
She also credited the Charlie Hustle team with prioritizing authenticity, from fabric selection to embroidery choices, ensuring that the final product reflected both the brand’s heritage and her own standards.
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Haines Eason is the owner of startup content marketing agency Freelance Kansas. Previously he worked as a managing editor for a corporate content marketing team and as a communications professional at KU. His work has appeared in publications like The Guardian, Eater and KANSAS! Magazine among others. Learn about him and Freelance Kansas on LinkedIn.
