Retailers at Chicago Collective Ready to Tackle Everything from Hybrids to AI

Department store bankruptcies, tariffs, shifting consumer tastes — these are just a few of the issues facing independent retailers in 2026. But by sticking with the tried-and-true strategies that have been their hallmark, men’s merchants believe they can overcome any obstacles thrown at them and continue to prosper.

Retailers shopping the Chicago Collective menswear show last week were in fine spirits after a solid holiday season. And they were writing orders to finalize their fall 2026 buys in anticipation of continuing the momentum.

While tailored clothing continued to represent the bulk of sales for most stores, the popularity of luxury sportswear — led by the quarter-zip in an array of materials — and hybrid silhouettes increasingly attracted attention at the market. The heritage and preppy aesthetic also gained fans, while trousers, most with pleats and a looser silhouette, will give retailers more fuel to boost sales later this year.

All told, the show drew 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. “Just when we think it can’t get any better, attendance is up 9 percent over last year. We are incredibly grateful to our partners, exhibitors and retailers — we couldn’t do this without them.” The next show will take place Aug. 1 to 4.

The Chicago Collective continues to be the must-attend show for independent menswear stores to find trend-right merchandise while reconnecting with their contemporaries about how best to navigate the macro-issues facing the industry.

“We ended our fiscal year at the end of January and we beat plan,” said Richard Penn of the three-unit Puritan Cape Cod chain. The company also operates a Vineyard Vines store. While the beginning of 2025 was slow due to tariff uncertainty, by May, that dissipated and customers returned to shopping.

At the show, he was looking for some “new and exciting elevated sportswear. The days of men wearing suits every day is over.”

Keith Kinkade of Kinkade’s in Ridgeland, Miss., said his sales ended up 5 percent in 2025 and he was optimistic about this year. The store has always had success by staying connected with the local community and creating some innovative promotions, such as giving away umbrellas in April, pecan pie for Thanksgiving and cinnamon rolls for Christmas. “We like to think a little outside the box,” he said.

At the show, he was shopping Gen Teal, one of his most popular sportswear brands, along with Mavi and Duck Head.

Peter Leff, executive vice president of wholesale at Tommy Bahama, said most of his retail customers posted strong sales in 2025, with particular strength in November and December. As a result, they were buying aggressively at the Chicago market. For his brand, bottoms continue to be extremely strong sellers, along with shirt jackets and sweaters as well as corduroy and flannel shirts, many in pop colors. “People want color, even in fall,” he said.

In addition to American brands such as Tommy Bahama, the Chicago Collective boasts a large contingent of Italian vendors, sponsored by that country’s Italian Trade Agency. This edition, the group managed to bring eight new brands and snag another two booths, bringing its total to 64 brands across a wide range of categories.

Alessio Nanni, head of the ITA’s beauty and fashion division, said Italian brands continue to clamor to get into the popular show to meet retailers they believe can best present their collections. To promote those relationships, the ITA hosted a cocktail party Monday night and also offered drinks and snacks each day on the show floor.

Beyond the espresso and aperitivo, Nanni said that while tariffs were the big concern at the show last year, they’re not as worrying now — especially among the brands showing. “At this price point, just under luxury, they don’t feel the effects a lot,” he said. “But we will see what happens in the future.”

Tariffs weren’t the only talking point for retailers, who were also grappling with several non-industry-related issues that could potentially impact business.

“In September 2020, we weren’t sure if anybody was going to wear suits again,” said Dan Orwig, president of Peerless Clothing, during a panel discussion hosted by WWD at the show. “But the key is really versatility and continuing to offer the guy different ways to wear product — from the comfort to the styling. It can’t just be for an occasion. You have to be able to wear it in a lot of different ways.”

Ken Giddon, president of Rothmans, agreed. In the past, about 70 percent of sales in his stores came from tailored clothing, but that number has dipped to around 50 percent, he said, as guys are “flooded with information on their social media” showing them how to dress differently.

Brian Cohen of Harpers men’s store in State College, Pa., said the percentage of tailored clothing he sells is probably closer to 60 percent. “I’m in a college town right across from Penn State, and we see a lot of young men, college men, buying their first suit. So if a young man’s coming in our store, he’s looking for something classic, traditional, for a career fair or going to an interview.”

John Totolis, director of retail strategy at DLS Outfitters, an advisory firm for specialty retailers, said that while classic will always have a place, brands are evolving to meet the demands of today’s man, offering options that are “a little bit cooler, a little bit looser, a little bit hipper,” and retailers should take notice.

“I think there’s this whole white space out there where it’s a classic guy that’s evolved, or he’s got too many shirts or too many five-pockets, or too many sport coats,” Totolis said. “You should do yourself a favor and start looking at these new, cooler brands.”

Whether the merchandise is classic or updated, the secret sauce for independent men’s stores continues to be their relationships with customers. Giddon, whose store is celebrating its centennial this year, said: “We don’t think of ourselves as a store. We think of ourselves as a hospitality platform. The first thing I tell new staff is, don’t ever ask anybody: ‘Can I help you?’ Because the answer is, ‘Just looking.’ We’re always about making them feel at home first. That’s what we can do that you can’t do online.”

Cohen said that Harpers, which is also 100 years old this year, strives to make its customers comfortable enough to just come in and visit without necessarily buying anything. “We have a foosball table, a couch, and the young guys will just hang out. In today’s world, especially with the internet, that’s a real measure of success.”

Customers today are bombarded with brands on their Instagram feeds, creating a new competitor. But even more concerning to many stores are the vendors who opt to sell directly to customers, either online or through their own stores. But retailers are finding ways to battle these newfound adversaries.

“We introduce a brand and we’re the first or second store in the country to carry it — people have never heard of it, and we’re building their brand,” Giddon said. “And then a year or two later, they’re hitting all of your customers with geo-locating while they’re in your store, with ads for that brand. So you develop a thick skin, and come to trade shows like this looking for the next guy.”

Cohen added: “You’re helping develop the brand, and then having to compete with them is no fun. So we have to decide when to cut them loose. You’re not special in my store anymore. And those are hard decisions.”

One strategy is to create private labels that can’t be replicated elsewhere. “Some of these stores have such a great following and the customers believe and trust in them so much,” said Orwig, whose company creates private label for several companies. “But I think you have to have a balance of branded business and private label.”

Whether national brands or private labels, Totolis said the rules of retailing have changed today which requires independents to plant a stake in the ground.

“When I grew up, great product was all you needed,” he said. “Then it was great product and customer service. Now, it’s great product, customer service and marketing. And your job is figuring out: what are the programs, the styles, the vendors that we’re going to bombard our customer with. Put them in the window, put them on the front table. Buy with conviction. Put them on Instagram, Facebook, TikTok, e-mail blasts, because that’s going to trigger your marketing strategy where you can compete with these direct-to-consumer people.”

He said stores shouldn’t be shy about putting themselves out there to customers. “You should be doing Ken’s picks, Brian’s picks — customers love the buyers’ picks. You’re the owners of the store, trust me, they’ll listen,” said Totolis.

The discussion then turned to AI and the panelists said they were all using it in some form. Giddon said he uses ChatGPT to answer questions he might have hired a high-price consultant to answer in the past. Orwig said his company has found it useful in the design process where tweaks can be made in seconds as well as for data analysis. Cohen said he uses it to create images for his website.

Totolis said: “If you read the media, they’ll make it sound like everyone’s using AI except for you. We talked to a lot of stores, and no one’s really using it to gain more customers. But where they are using it is imagery.”

Finally, the panelists also addressed the issue of tariffs. “Tariffs are like hot dogs,” Giddon said. “You know they’re bad for you, but you don’t know what’s inside.”

Orwig said that the Canada-based Peerless passed along some of the increases and absorbed the rest but “the consumer hasn’t really stopped buying based on those increases.” And Totolis said retailers shouldn’t worry too much about passing along the added costs, as long as they maintain the price ranges their customers have come to expect.

Here, some of the key brands that showed at the fall market:

Bosca

Amy Luther has big plans for Bosca, the 113-year-old Italian-American heritage accessories brand she recently acquired. The entrepreneur and Springfield, Ohio, native had been a fan of the company since she worked in the handbag department at Macy’s early in her life. But after building and selling a successful human resources consulting firm, Luther was looking for her next chapter, and found Bosca.

She befriended Chris Bosca, the fourth generation of the founding family, who agreed to sell the business. Now her plans call for building the brand’s core men’s leather goods and expanding into women’s this summer.

Although the brand had at one time manufactured in the U.S., most of its production today is in Italy. Luther hopes to change that in the third quarter of this year by returning some of the production to Springfield.

Luther said that what sets Bosca apart from other leather goods brands is its hand-stained, vegetable-tanned and highly polished finishes that develop a desirable patina as they age. Wallets in a variety of models, including bifold, trifold and front pocket, along with card cases are among the bestsellers. Wallets average between $140 to $200 retail.

At the show, the company offered a range of these products along with bags, dopp kits, portfolios and belts. Luther said that in response to demand from younger customers, the men’s bags are being made smaller as the amount of paper and other products guys carry around today is not as bulky.

Johnnie-O

It all started when John O’Donnell created a logo of a guy standing on a beach holding a surfboard that he put onto a golf shirt. In the past 21 years, that nascent brand has grown into a $200 million-plus business selling a full range of men’s, women’s and kids’ apparel and accessories from shoppers seeking a blend of East Coast preppy and California casual.

In recent years the company has also moved into a more-elevated offering that it calls Top Shelf, which now spans sport coats, button-down shirts, knitwear, outerwear, five-pocket pants and garment-dyed trousers.

At the Chicago Collective, it was the Top Shelf line that attracted much of the attention. Michael Lamaker, senior vice president of sales, specialty, stressed that its positioning doesn’t mean the collection is more expensive. “It’s just dressier — we still offer a lot of value.”

He pointed to the quarter-zips in a cashmere blend with faux suede zippers and detailing that retails for $998. A vest and a full-zip jacket in Loro Piana Storm System fabric sell for $998 and $1,298 respectively. Other key pieces for fall include merino-silk-cashmere sweaters with a French placket that can be worn under a sport coat as well as “everybody’s favorite Christmas gift,” Lamaker said: a 100 percent cashmere sweater, one of which was available in an innovative honeycomb effect texture, for $398.

For those still seeking the line’s heritage products, Johnnie-O still offered a wide assortment of golf apparel as well as a Lodge collection of casual sportswear.

Luigi Bianchi

A division of the Mantova, Italy-based Lubiam, the company was founded in 1911 by Luigi Bianchi, an Italian tailor who started his training in Turin at the age of 16 before opening his own workshop.

Today, Lubiam is one of the oldest Italian fashion companies still owned by the founding families and it creates collections under both the Luigi Bianchi and L.B.M. 1911 labels.

For Luigi Bianchi, whose Made in Italy half-canvas construction is the “more sartorial” offering from the company, the fall collection was titled Gentle Shades, as evidenced by the palette of dusty natural shades, cool green and deep black.

Although suits and sport coats remain the backbone of the collection, it is “becoming much more lifestyle,” said Marc Spero, president of Lubiam USA, with knitwear, outerwear and accessories in alpaca blends, mohairs and brushed wools gaining importance.

Among the key pieces for fall were a hooded jacket in Loro Piana Storm System fabric and a knee-length car coat with an inset vest. Spero said vests, which were offered in a range of styles including quilted options, is a new category for the brand. Other highlights included double-breasted peacoats, cashmere blousons with exaggerated envelope pockets, overshirts in a wool-cashmere blend and pleated trousers in different styles.

Manto Italia

The luxury Italian men’s brand is doubling down on its commitment to the U.S. market.

Founded in 2016, the company designs, develops and manufactures its collection in its home country, partnering with specialized Italian workshops for category-specific expertise. Leather jackets are made by leather ateliers, technical outerwear by experts in performance fabrics; double-face fabrics are created by workshops that focus almost exclusively on this complicated technique.

“For us, Made in Italy is not just a label — it is a responsibility,” said Antonella Arpaia, cofounder and creative director. “Every Manto garment is designed, developed, and produced entirely in Italy, allowing us to follow each piece from the initial idea to the final product. This complete control over the process is what gives our collections authenticity, consistency and true value.”

The fall collection, which was also shown at Pitti Uomo, included knit jackets and overshirts in fine-gauge fabrics with a light internal membrane that was soft but still maintained its structure; a North American buffalo suede jacket with a custom check print; double-face cashmere chore or double-breasted coats; unlined Donegal tweed jackets, and a double jacquard featuring a lotus motif, a signature of the brand and its hometown of Manto. Prices range from $1,295 to $3,495.

Although the collection was ostensibly fall, the brand follows a non-seasonal approach with most garments light enough to be worn in cool temperatures or as layering pieces in the cold.

Peter Millar

It was 25 years ago that Greg Oakley, Chet Sikorski and Chris Knott started a brand with a single cashmere sweater offered in a variety of colors. In addition to that sweater, Peter Millar’s early success came in golf, but today, the company has grown into a full lifestyle brand for men, women and children that eventually caught the eye of the luxury conglomerate Compagnie Financière Richemont, which acquired it in 2012.

While golf remains a key category for the brand, lifestyle products represent around 75 percent of its overall business today, according to Jason Cater, chief creative officer. “We blur the lines between lifestyle and performance,” he said, pointing to wind- and water-resistant cardigans and a zip-up with wool-polyester sleeves and a nylon chest that can be worn on or off the course.

Other key pieces include a reversible vest and a quilted down alternative coat in a wool-cashmere stretch material. Cater said that two years ago, Peter Millar began offering sport shirts in a cotton-nylon-spandex fabric that looked like a traditional dress shirt but “in your favorite polo fabric.” The shirts, which are available in solids as well as stripes and a printed gingham pattern, are washable and retain their shape. They retail for $275.

The brand also offers some tailored options including a wrinkle- and water-resistant Excursionist Flex blazer that is unlined but features stretch. Cater said the model is the brand’s top seller.

Peter Millar offers the popular Crown collection of casual weekend attire that includes stretch corduroy shirt jackets, padded vests and quarter-zips, cotton-cashmere field jackets, performance flannel button-downs, Fair Isle sweaters and a cotton-cashmere field jacket.

In celebration of its anniversary — and a nod to its initial product — the company in September will be introducing a cashmere quarter-zip in 16 colors that will sport the original label and hang tag along with special hand-stitched XXV in orange. Other special pieces will also be offered in limited numbers.

Polo

Preppy, heritage, Americana — all trends for the fall 2026 season. But that’s just what Polo Ralph Lauren has been doing for decades, making the brand more popular than ever.

At the Chicago show, the company filled a booth with all the key messages of the season, broken down into several categories: Heritage Preppy, Refined Sportswear, Red Rocks, a mix of denim and active, and Royal Holiday.

Key pieces included tweeds mixed with Fair Isle sweaters, soft sport coats and dress trousers — “classic Americana,” said Bill Huntington, head of menswear, childrenswear and golf North America wholesale. The message was driven home by flag sweaters, wool Shetland sweaters, twill or flannel sport shirts and rugbys in a variety of colors. Corduroy sport coats, chore jackets and chinos in a more-baggy silhouette were also offered.

Leather jackets, both in distressed finishes or traditional moto styles, were part of the line, and there was a push into tailored clothing with wool-blend or corduroy sport coats, corduroy pants with side tabs, a suede Baracuta jacket and a reversible suede shirt jacket. “Classic Ralph, put together for the next generation,” Huntington said.

The holiday offering featured a Black Watch shirt jacket, a high-pile fleece jacket, bear sweaters, a wool-cashmere tartan sport coat, velvet pants and cashmere turtlenecks.

The Red Rocks assortment included flannel workshirts, a “new take on the rugby,” with quilting on the shoulder and hunting pockets on the back, and even a camo jacket, Huntington said.

The collection made its debut in Milan during men’s fashion week, sharing the runway with the upscale Purple Label collection.