While fast fashion churns through micro-trends at breakneck speed, a handful of menswear businesses are quietly celebrating milestones that most retailers never see. The average company has roughly a one-in-three chance of surviving a decade, yet four family-run operations gathered at last week's Chicago Collective trade show with a combined 332 years of experience between them. Their conversation, moderated by WWD's senior menswear editor Jean E. Palmieri, offered a masterclass in endurance that goes far beyond fabric choices. Main Developments The panel brought together two retailers and two manufacturers who have each cracked the code of longevity in dramatically different ways. Cecile Revah of Bugatchi joined as the shirtmaker celebrates its 45th anniversary, while Gina Zangrillo represented Darien Sport Shop at 80 years. Ken Giddon of Rothmans marked a full century in business, and Douglas Raicek from Peerless Clothing rounded out the group as the elder statesman at 107 years old. Resilience emerged as the first pillar of survival, with Giddon recounting how his grandfather-founded Union Square retailer has weathered everything from Sept. 11 to superstorm Sandy, the COVID-19 pandemic, and even looting. "We've been through everything, and we just keep getting back up," he said, framing each crisis as another chapter in a century-long story of persistence rather than a reason to close up shop. Read also: Jo Malone London Enters Gaming With Fortnite Fragrance Launch Customer service, not hype, formed the second theme. Giddon proudly noted that Rothmans, which began as a discounter, has never chased a seat at the "cool table" — and he offered a pointed example. An annual New York Times list of the city's top 50 clothing stores never includes Rothmans, and Giddon finds that amusing because "half those stores are gone" by the time the next list comes out. His family's focus instead remains on excellent service, a value that has outlasted countless trendier competitors. Revah echoed that sentiment from the manufacturing side, crediting feedback from key stockists like Rothmans for persuading her to expand Bugatchi from a shirtmaker into a full lifestyle collection. "I think that what's important is to always keep your ears open, to always have something new," she said, though she carefully distinguishes newness from chasing trends. Whether introducing a fresh colorway or venturing into an entirely new category, the goal is expanding how customers can engage with the same brand story. Raicek framed the third lesson around adaptability, noting that Peerless Clothing — North America's largest suit producer — still makes essentially the same tailored garments it did a century ago. What has changed dramatically is the path to production, with increased reliance on Chinese manufacturing and fluctuating tariff policies under President Donald Trump forcing constant recalculation. "Staying on top of it has forced us to constantly rethink the business and evolve," he said. The fourth lesson came with a dose of humility from Zangrillo, who admitted that her biggest struggle at Darien Sport Shop involves competing with brands she helped build. She recalled when Vineyard Vines founders first walked in "with a knapsack of ties," and her store bought everything they made, growing that business to an estimated $2 million to $3 million. Then the brand opened stores on both sides of her Connecticut shop, forcing a strategic reckoning about when to ride a wave and when to step aside. Background These longevity stories stand in stark contrast to broader business survival statistics. Nearly half of all businesses never reach their fifth anniversary, and only about one-third make it to the 10-year mark — making the panelists' combined track record all the more remarkable. Each company took a different route to endurance: Rothmans started as a discounter, Peerless built scale as a suit manufacturer, Bugatchi grew from a niche shirtmaker, and Darien Sport Shop remained a community-focused independent retailer. Family dynamics thread through several of these operations. Giddon's grandfather founded Rothmans, and he now works alongside his brother Jim, navigating both the joys and pitfalls of family business. The panel touched on this dynamic, along with the arrival of artificial intelligence, which everyone at the table is embracing primarily for data analysis rather than creative work. The conversation also revealed how these businesses view the trade show circuit as essential to their survival strategy. Giddon returns to Chicago Collective twice annually with a specific mission: "to find the next guy that we're gonna help create." His team arrives with appointments scheduled from Saturday at noon through Tuesday at three, and he described the process as an active hunt rather than passive browsing. Why It Matters For an industry increasingly dominated by rapid trend cycles and digital disruption, these four businesses offer a counte