The Casey Adams Show
Chris Riccobono – Founder of UNTUCKit on How He Built One of the Most Recognized Brands in Modern Retail
May 2, 2025
Chris Riccobono, the founder of UNTUCKit, turned a simple frustration with shirt fit into a retail revolution with over 80 stores. He discusses how storytelling and brand differentiation foster customer loyalty. Chris explores the ongoing evolution of retail, the impact of e-commerce on consumer behavior, and the challenges of balancing fatherhood with entrepreneurship. He also shares insights on launching Greatness Wins and navigating the trials of building a brand during the pandemic.
47:04
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Quick takeaways
- Chris Riccobono identified a gap in the market for untucked shirts, transforming his personal frustration into a successful retail brand.
- Balancing entrepreneurship and fatherhood, Riccobono emphasizes creating boundaries while leveraging flexibility to instill a strong work ethic in his children.
Deep dives
The Inspiration Behind Untuckit
The concept for Untuckit arose from Chris Riccobono's realization that men's shirts were consistently designed to be worn tucked in, despite a demand for shirts that could be worn untucked. During his college years, he observed a shift from oversized clothing to more fitted styles, yet he found that many shirts were still unflatteringly long for shorter wear. After conducting a survey in Hoboken, he confirmed that 95% of men felt this was a significant issue. Motivated by his personal need for shorter shirts, Chris combined his entrepreneurial spirit with the potential of e-commerce to address this gap in the market.
