UNTUCKit: Chris Riccobono

What It Covers

Chris Riccobono built UNTUCKit from zero fashion experience into a brand with 80+ stores by solving one problem: dress shirts designed to be worn untucked at 28.75 inches length, nearly selling for $750 million before COVID.

Key Questions Answered

• •Manufacturing quality control: Cotton fabric grows and shrinks unpredictably, requiring pre-washing and strict length specifications within fractions of an inch. Most brands allow 2-3 inch variances because tucked shirts hide length inconsistencies, but untucked shirts demand 28.75-inch precision every time or the entire concept fails.
• •Naming as competitive advantage: Choosing a descriptive, non-sophisticated name like UNTUCKit over an Italian-sounding brand name enabled billboard advertising with just the name and tagline. The simplicity allowed instant comprehension and became synonymous with the category, like Kleenex for tissues, despite fashion industry ridicule.
• •Slow growth survival strategy: Growing from $90,000 to $300,000 to $500,000 over three years with terrible initial product quality allowed time to perfect manufacturing before scaling marketing. Keeping customer lists from bad batches enabled future outreach when quality improved, turning early failures into eventual wins without destroying the brand.
• •Alternative marketing channels: Radio sports shows, Howard Stern, airline magazines, and billboards returned measurable revenue when competitors focused solely on paid social media. Testing each channel with small budgets and tracking direct conversions identified profitable channels that established brands ignored, enabling growth with minimal venture capital.
• •Wholesale timing strategy: Delaying wholesale partnerships until establishing direct-to-consumer brand strength and profitable operations creates negotiating leverage. Entering Nordstrom and Macy's after proving customer demand through 90 owned stores positions the brand as a proven winner rather than a desperate startup seeking distribution.