You probably remember the voice before you remember the face. It was deep, gravelly, and carried a weirdly comforting authority. George Zimmer didn't just sell suits; he sold a version of confidence that felt accessible to every guy who walked into a mall. For decades, he stood in front of a camera and promised, "You're going to like the way you look. I guarantee it." Then, in June 2013, the guarantee suddenly expired.
The story of George Zimmer and Men's Wearhouse isn't just a corporate history lesson about a guy getting fired from the company he built from a single cigar box. It’s a messy, fascinating case study in what happens when a founder's "soul" for a brand hits a brick wall made of boardroom spreadsheets and corporate governance.
The $25 Million "Ambush"
Most people think George Zimmer just retired. He didn't. He was fired.
On a Wednesday morning in 2013, the board of directors released a three-sentence statement that basically nuked the company’s identity. They terminated Zimmer as executive chairman. No explanation. No "thank you for your service." It was so abrupt that the Men’s Wearhouse website still had his face plastered all over the homepage for hours after the news broke.
Honestly, it was a total disaster from a PR perspective.
Why did it happen? The board eventually claimed Zimmer was obsessed with "full control." They said he was making it impossible for the new CEO—a guy Zimmer actually handpicked, Doug Ewert—to do his job. But if you ask Zimmer, he’ll tell you he was pushed out because he was vocal about the company’s soul. He didn't want to sell off certain divisions (like K&G Fashion Superstore), and he was reportedly pushing back against massive executive pay raises while the company was struggling to find its footing after the 2008 recession.
From a 1973 Suitcase to a Multi-Billion Dollar Empire
To understand why the firing hurt so much, you have to look at where Men's Wearhouse started. Zimmer wasn't some Ivy League MBA. In 1973, he and some college roommates opened the first store in Houston. Back then, they used a cigar box as a cash register.
Zimmer’s philosophy was "stakeholder capitalism" before that was a buzzword. He did things that drove traditional corporate types crazy:
- No criminal background checks: He believed in second chances.
- Employee-centric culture: He focused on the people on the floor, not just the shareholders.
- The "I Guarantee It" Slogan: He started doing his own commercials in 1986 because he couldn't afford a real actor. It turned out to be the best marketing move in retail history.
By the time he was ousted, the company had over 1,200 stores. It was the king of the "regular guy" suit. But being a public company changes things. Once you're on the NYSE, your "gut feeling" and "values" are often viewed as liabilities if they don't align with quarterly growth projections.
The Post-Firing Pivot: Generation Tux
A lot of guys in their 60s would have taken their $67 million in stock and disappeared to a beach in Hawaii. (Which he did, briefly—he actually owned an incredible estate on the Big Island.) But Zimmer is a merchant at his core.
He didn't just ride off into the sunset. He got mad, then he got busy.
He launched Generation Tux and zTailors. He basically realized that the "three trips to the mall" model for renting a tuxedo was dead. Millennials didn't want to go to a physical Men's Wearhouse store. They wanted to do it from their phones.
"I knew that if I could develop something... my maturity and wisdom would enable me to be more mellow the second time," Zimmer told the Glossy Podcast.
Generation Tux became his "second act." He used $20 million of his own money to get it off the ground. It was a digital-first version of what he spent 40 years building. Instead of a guy in a warehouse measuring your inseam, you had an algorithm and a high-tech shipping facility in Louisville.
What Most People Get Wrong About the Breakup
There’s a common misconception that Men's Wearhouse failed because George left. That's not quite right. The company actually merged with Jos. A. Bank shortly after he left, creating a massive conglomerate (Tailored Brands).
The real failure was a loss of identity.
When you remove the founder who is the brand, you're left with a hollow shell. They tried to replace him with different spokespeople, but nobody could replicate that gravelly sincerity. The company eventually filed for Chapter 11 bankruptcy in 2020 during the pandemic—though they've since emerged. Zimmer, meanwhile, was busy scaling a business that didn't have the overhead of 1,200 leases.
Why George Zimmer Still Matters in 2026
If you look at the landscape of business today, Zimmer’s "hippie capitalist" vibe is actually the standard. Every brand wants to talk about their "values" and "social impact." George was doing that when it was considered a liability.
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He’s currently living in Oakland, focusing on his businesses and his philanthropy (he’s a big supporter of the Oakland Zoo). He even wrote a memoir titled I Guarantee It, where he finally spilled the tea on the boardroom betrayal.
Lessons From the "I Guarantee It" Guy
If you’re a founder or a business leader, the George Zimmer Men's Wearhouse saga is a warning.
- Ownership is everything. Zimmer only owned about 3.5% of the company when he was fired. If you go public, you serve the board, not the other way around.
- Values are a competitive advantage. People shopped at Men's Wearhouse because they trusted George. When the trust left, the brand became just another clothing store.
- Adapt or die. Zimmer’s move to Generation Tux proves that even an "old school" guy can see the writing on the wall regarding e-commerce.
To really follow in Zimmer’s footsteps, you don’t need a deep voice or a beard. You need to understand that the "guarantee" isn't a marketing trick—it's a promise to the customer that you'll stand behind the product.
For your next move, check out Zimmer’s book I Guarantee It to see the specific legal and corporate maneuvers that led to his exit. It’s a masterclass in what not to do when structuring a board. If you're looking for a suit today, compare the online fit technology of Generation Tux against the traditional in-store experience; you'll see exactly how he's trying to disrupt the empire he originally built.