Independent retailers are navigating a challenging landscape in 2026, grappling with department store bankruptcies, tariffs, and evolving consumer preferences. Nevertheless, men’s merchants are optimistic, banking on traditional strategies to remain resilient and continue their success. At the recent Chicago Collective menswear show, attendees expressed enthusiasm after a solid holiday season, placing orders to secure fall 2026 merchandise amid positive momentum.
While tailored clothing remains the cornerstone of many stores, luxury sportswear—especially quarter-zips across various materials—and hybrid silhouettes are capturing increased attention. The heritage and preppy styles have seen a resurgence, while trousers featuring pleats and relaxed fits are expected to enhance sales this year. The event attracted a record 1,200 buyers, including retailers from Canada, Japan, and Puerto Rico. “This was one of our best shows to date,” said Monique Kielar, vice president of marketing for the Chicago Collective, noting a 9 percent rise in attendance compared to last year. The next show is scheduled for August 1-4.
The Chicago Collective remains a pivotal venue for independent menswear retailers looking to discover trending merchandise and engage with peers about navigating industry challenges. Richard Penn of the Puritan Cape Cod chain, which operates three stores including a Vineyard Vines location, said his company exceeded its fiscal goals at the end of January, despite a slow start to 2025 due to tariff uncertainties. “By May, that dissipated, and customers returned to shopping,” he noted.
At the show, Penn sought “new and exciting elevated sportswear,” reflecting a shift away from daily suit-wearing norms. Keith Kinkade of Kinkade’s in Ridgeland, Mississippi, reported a 5 percent sales increase in 2025 and is optimistic moving forward. His store has thrived by engaging with the local community through innovative promotions, such as holiday giveaways and seasonal gifts. At the event, he explored options from popular brands like Gen Teal, Mavi, and Duck Head.
Peter Leff, executive vice president of wholesale at Tommy Bahama, highlighted strong sales among retail customers in 2025, particularly in November and December, leading to aggressive buying at the Chicago market. He noted that bottoms, shirt jackets, sweaters, and corduroy and flannel shirts—often in vibrant colors—are maintaining popularity. “People want color, even in fall,” he said.
The Chicago Collective also featured a significant presence of Italian vendors, supported by the Italian Trade Agency, which introduced eight new brands this year. Alessio Nanni, head of the ITA’s beauty and fashion division, emphasized that tariffs have become less of a concern compared to the previous year, particularly for brands at a sub-luxury price point. “They don’t feel the effects a lot,” he remarked, though he acknowledged uncertainties ahead.
Retailers at the show discussed various macro issues impacting business beyond tariffs. Dan Orwig, president of Peerless Clothing, noted that adaptability is key, emphasizing versatility in men’s fashion. His observation reflected a change in consumer habits influenced by social media trends. Ken Giddon, president of Rothmans, shared that tailored clothing sales dropped from 70 percent to about 50 percent as men are increasingly exposed to diverse styling options online.
Retailers like Brian Cohen of Harpers men’s store in State College, Pennsylvania, noted a different dynamic in college towns, where young men often seek classic styles for interviews and formal occasions. John Totolis, director of retail strategy at DLS Outfitters, suggested that while classic styles remain relevant, brands should adapt to meet today’s male consumer, introducing cooler, more relaxed options.
Giddon described independent stores as hospitality platforms rather than mere retailers, focusing on nurturing customer relationships. For instance, Cohen’s store, which also marks its centennial this year, creates an inviting atmosphere that encourages customers to linger, regardless of whether they buy anything. “In today’s world, especially with the internet, that’s a real measure of success,” he said.
However, independent retailers face competition not only from traditional rival stores but also from brands that sell directly to consumers. Giddon expressed frustration over brands he helped establish later targeting the same customers through geo-marketing. He suggested retailers might need to develop private labels to maintain exclusivity. “You have to find a balance between brand and private label,” he urged.
The panelists acknowledged the necessity of evolving retail strategies to remain competitive. “When I grew up, great product was all you needed,” Totolis remarked. “Now it’s great product, customer service, and marketing.” He stressed the importance of proactive engagement with customers through social media and personalized promotions, leveraging buyer recommendations to build stronger connections.
On the technological front, all panelists reported utilizing AI in some capacity, with Giddon using ChatGPT for inquiries typically addressed by consultants. Orwig highlighted AI’s role in the design process, enabling rapid adjustments and data analysis, while Cohen noted its utility in website imagery. However, Totolis pointed out that while discussion of AI is prevalent, few retailers have effectively harnessed it to attract new customers.
As retailers navigate tariffs and changing consumer behaviors, Giddon likened tariffs to “hot dogs,” acknowledging their complexity and hidden implications. Orwig indicated that while Peerless absorbed some tariff increases, consumer spending remained steady, and Totolis advised that passing along costs should be manageable, provided retailers maintain expected price ranges.
Looking ahead, the upcoming fall season promises a mix of classic and evolving styles, as independent menswear shops adapt to meet the diverse needs of their customers while cultivating relationships that differentiate them from online competitors.
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