UNTUCKit: how a non-fashion guy built a brand around one shirt length

Executive overview

Most dress shirts were designed to be tucked in — so when worn out, they looked sloppy and too long. Chris Riccobono spotted this gap, spent two years figuring out how to make a shirt at exactly the right length, and built a brand around a single, polarising idea.

Neither Chris nor his co-founder Aaron Sanandres had fashion experience. They kept their day jobs for years, shipped from an apartment, fixed defective inventory by hand, and grew slowly enough to get the product right before scaling. That frugality almost didn't survive COVID, when a near-$750M acquisition collapsed overnight.

The name was the brand: "Untuckit" told customers exactly what the product was, made competitors easy to spot, and became the generic term for the category — worth more than any ad.

The idea and early years

• Chris spent a decade at GE in medical sales, knowing early he wouldn't advance in corporate America
• Did an executive MBA at Columbia; met co-founder Aaron Sanandres there
• Tried multiple failed ventures: a wine vlog, an online dating site for little people, reality TV scripts
• The untucked shirt idea crystallised in Las Vegas — friends validated it with genuine excitement, not polite interest
• Aaron, a PwC partner, said "I'm in" without hearing the full pitch — the first signal the idea had real pull
• Wandered New York's garment district with one J.Crew shirt, asking factories to copy it; most refused or said it violated standard specs
• Took two years to get to market; neither founder quit their day job

Getting the product right

• Core spec: 28.75 inches in length for a medium — if off by an inch either way, the shirt fails its only promise
• First batch from a Polish factory was defective: arms grew after washing while the rest shrunk; buttons were untied by a broken machine
• Sold the defective shirts anyway — refunded $5 per shirt and asked customers to visit a dry cleaner; kept every customer's name
• Survived early quality failures only because growth was slow — fixed the product before marketing it at scale
• Found Bjorn, a veteran garment expert at the Fashion Institute, who spotted the quality issues and joined to fix them
• Implemented strict quality control: washing each yard of fabric before cutting, rejecting anything out of spec — initially factories refused; Chris held the line

Building the business without money

• Raised ~$150K from friends and family to start; kept overhead near zero — shipped from a Hoboken apartment until 2015
• Ironed and hand-packed shirts at home, sometimes until midnight
• Revenue grew slowly: ~$90K, $300K, $500K in the first three years, then $3M to $15M
• First marketing breakthrough: $21K on Boomer & Carton sports radio, New York — a thousand site visitors within 20 seconds of the first read
• Airline magazines proved highly effective: spent $15K, made $45K — the placement made Untuckit look like an established brand
• Expanded to Howard Stern; tested billboards, podcasts, print; tracked ROI closely and doubled down on what returned

The name and brand strategy

• Chris coined "Untuckit" walking outside his parents' house; most advisers told him not to use it
• The name was almost weaponised against them — people assumed a gimmicky name meant a gimmicky product, raising the bar on quality
• Comedians and late-night hosts mocked it (Seinfeld, Letterman, Colbert, Kimmel, Gaffigan) — all free publicity that drove curiosity
• GQ and fashion press ignored them for years; Chris saw this as validation they were building something outside the establishment
• By 2019, every major competitor — J.Crew, Banana Republic, Vineyard Vines — launched campaigns with "shirts designed to be worn untucked"; two copied the exact phrase and had to remove it

Fundraising and growth

• Raised $8M from Kleiner Perkins in 2016–17 (total round ~$30M including secondary); Kleiner saw them as a potential great American brand, not just an apparel play
• Opened first store in SoHo in 2015–16; worked the floor daily; store performed so well they opened 90 stores in roughly two and a half years
• Kept majority equity by taking on debt rather than repeated equity rounds — Kleiner actively encouraged minimal dilution
• Reached ~$53M in revenue with lifetime fundraising of ~$9M on the balance sheet

The near-acquisition and COVID collapse

• Late 2019: tested the market for acquisition; received 15 letters of intent at valuations north of $750M
• March 2020: every potential acquirer withdrew — COVID shut the process down overnight
• Revenue dropped 40–50% as stores closed; accounts payable to factories was tens of millions; had already ordered inventory for a high-growth year
• A bankruptcy attorney told Chris and Aaron to declare — they would have lost nearly all equity
• Instead: called every landlord and factory one by one; 90% agreed to restructure rather than see the brand fail
• Raised emergency capital at a low valuation (Kleiner participated again); took on additional debt to bridge

Recovery and current state

• Post-COVID, the brand returned to profitability in 2022 and had its most profitable year in 2023
• 2025 described as an "exciting year" with strong growth; entering wholesale through Nordstrom, Macy's, Stitch Fix
• Expanding internationally: Canada performing well, England launched, Mexico City store planned
• Women's line and trousers growing with minimal dedicated marketing
• Chris and Aaron still targeting an eventual acquisition to establish the brand long-term; Chris is explicit that financial return is a core goal, not just mission