That’s Ken Giddon, on why his family’s menswear shop Rothmans has made it 100 years. He said it on a panel of four long-running menswear businesses at Chicago Collective this month, a combined 332 years between them. Nearly half of new businesses don’t survive their fifth year. About a third reach year ten.
WWD’s Jean E. Palmieri moderated the panel at Chicago Collective, the menswear trade show we covered a couple of weeks back. The four panelists: Cecile Revah of Bugatchi (45 years), Gina Zangrillo of Darien Sport Shop (80 years), Ken Giddon of Rothmans (100 years), and Douglas Raicek of Peerless Clothing, the oldest of the group at 107. Asked how to last that long without going stale, each gave a genuinely different answer.
A disaster recovery, a tariff-driven supply chain rebuild, a shirtmaker turned lifestyle brand, and a shop that kept selling a line that became its own competition don’t look like the same story. Read them side by side and they share a shape: each business let almost everything change, sourcing, category, geography, even who’s selling next to them, while holding one thing fixed. For Rothmans, that’s the service and the refusal to chase trend-press relevance. For Peerless, it’s the product promise itself. For Bugatchi, it’s the relationship with the retailers who carry the line. For Darien Sport Shop, it’s evidently not the account itself, but Zangrillo still selling Vineyard Vines after it became a rival says the relationship mattered more than the grudge.
Raicek’s line is the most transferable one on the panel. The “same product” in a bespoke or made-to-measure shop is the fit and the craftsmanship a client is actually paying for. Everything else, which supplier you use, how you track a client’s measurements and history, whether that record lives on paper or in software, is the “how,” and it’s allowed to change constantly without touching the promise underneath it.
That distinction gets tested hardest in the situation Darien Sport Shop lived through. Every tailor who trains an apprentice or builds up a supplier relationship is doing a version of what Zangrillo did with Vineyard Vines: helping someone else get good enough to eventually compete with you. Her answer wasn’t to cut them off. It was to keep the relationship and let the business around it change shape.
It shows up in smaller decisions too. A shop that switches wool suppliers because tariffs made the old one too expensive, the way Peerless has had to rethink sourcing, hasn’t changed what it promises a client, only where the cloth comes from. A shop that moves a client’s fit history off an index card and into software hasn’t changed what gets remembered, only how reliably it survives a staff change. The test in both cases is the same: does the client notice a difference in what they’re actually getting, or only in what happens behind the counter. If it’s the second, the change is safe. If it’s the first, it’s worth a harder look before making it.
The panel’s conversation eventually turned to AI, and the room’s answer was almost boring: all four are already using it, mostly for data analysis, not for anything that touches the customer directly. That’s a duller answer than AI usually gets in menswear coverage, and it’s worth taking seriously precisely because it’s dull.
“Data analysis” sounds abstract until you translate it into what a tailor shop this size actually has lying around in its own records. It’s the pattern in which regulars go quiet after a life event, a new job, a wedding, a weight change, that used to change what they needed and probably will again if you catch it early enough to ask. It’s noticing that the same alteration keeps coming back on the same block or the same fabric, which is a pattern problem worth fixing at the source, not a one-off fitting note. It’s timing a fabric reorder to what’s actually selling instead of what’s always been ordered. It’s reading which appointment slots turn into no-shows and which turn into rebookings, instead of assuming every open hour on the calendar is worth the same.
What makes this version of “going digital” worth doing is that it doesn’t ask a client to notice anything different. It’s about not losing track of things a good tailor already keeps in his head, the details that get fuzzier the busier a shop gets or the more staff turn over. That’s the “how” changing again, the same distinction Raicek drew about sourcing, applied to the shop’s own records instead of its supply chain. What a client actually experiences in the fitting room doesn’t move, it just gets harder to lose.
Four businesses, four different crises and openings, and the same underlying move: change nearly everything about how the business runs while refusing to change what it actually promises a customer. Write down the one thing your shop promises that can never change, no matter which supplier, tool, or trend comes and goes, and check whether every recent decision has actually protected it. That’s a sharper question than “should I modernize,” and one you can answer this week.
Quotes from Ken Giddon, Douglas Raicek, Cecile Revah, and Gina Zangrillo are drawn directly from WWD’s “Longevity Insights From Four Menswear Experts” by Ari Stark (August 10, 2026), reporting on a panel moderated by Jean E. Palmieri at Chicago Collective. The reading of a shared pattern across all four businesses is our own analysis, not a claim made by the panelists.
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