A textured jacket drapes his shoulders as he moves from beachside brunch to an afternoon luncheon. Later, custom leather Oxfords graze the hem of tapered linen slacks. The modern Southwest Florida gentleman’s style never sacrifices for comfort. His closet is tailored to his lifestyle.
A recent influx reshaping Southwest Florida’s restaurants, hotels and cultural life is also remaking wardrobes. “We’ve always had the wealth,” says Alexander Hayes, the Naples native behind Hayes Haberdashery—one of five specialty clothiers opened in the past few years. Now, he says, the social scene offers plenty of opportunities to step out in style. A night out at the new Olde Naples Hotel inspires mid-century whimsy with a sartorial edge, while the Florida-boho Canary Club calls for pure sprezzatura.
Menswear has expanded beyond the old plug-and-play formula of gray blazer, trousers and loafers. Knit polos, dress sneakers, shackets, softly tailored jackets and tonal separates offer a range of possibilities for the modern male wardrobe, making getting dressed more expressive—but also more complicated. “Men, for the first time, are admitting that they need help,” Alexander adds. Mostly, he explains, men are investing in clothes that complement the lives they lead.
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Photography by Erik Kellar
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Hayes Haberdashery owner Alexander Hayes (top photo) stocks niche Italian brands Stile Latino and Manto Italia.
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Photography by Christina Bankson
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One of the first pieces Craig DeLongy sold out of at John Craig Clothier in Naples this spring was a pink sport coat with a relaxed shoulder by Samuelsohn. After two decades in the local menswear scene, he’s watched men increasingly embrace personalization. “That includes three things: color, fabric and fit,” Craig says. In response, his new concept, The Collection by John Craig, opening on Third Street South this year, will offer an expanded made-to-measure section.
For the discerning gent, today’s shops marry expertise with club-like hospitality. Men seek out experiences, such as the Giorgio Armani pop-up event last season at Naples Beach Club, a Four Seasons Resort, and visit the resort’s Coastal Outfitters for its curation of ready-to-wear styles. At Tweeds in the Naples Design District—founded by Port Charlotte native Donald Carlson—buying a suit begins with a drink and ends with a round of putt-putt on the indoor green. Joseph Wendt Custom Clothiers, an early address for menswear on Broad Avenue South, pairs tailoring with an Italian wine and caviar bar. Suit Guy channels London’s sartorial culture, with brass accents and mid-century decor. “When you walk in my door, you’re going to be hit by a 1940s, 1950s Savile Row, Old World-style clothier shop,” says Suit Guy’s Aaron Gill, a fourth-generation tailor.
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Photography by Anna Nguyen
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At Joseph Wendt’s shop in Naples, guests grab a glass from the in-store wine bar.
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Photography by Anna Nguyen
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While staple pieces will always appeal to local men, in-house tailoring is du jour for the proper dressing den. A growing share of men want pieces not just fitted to them but cut to their specifications from the onset. Locals turn to longstanding boutiques, such as élevée by Rickey on Broad Avenue South in Naples. “Most clients come to us for event wear, but once you have something that fits your body, it’s hard to go back to ready-made,” says store manager Devon Kahn. Tweeds recently expanded its growing operation to Naples, and after years as a mobile clothier, Aaron opened his Suit Guy showroom in Fort Myers’ historic Richards Building in February.
The appeal lies in having a shopping experience where every detail is open to consideration. Joseph has spent over 30 years building wardrobes, including shoes from a Florentine cobbler he’s worked with for a decade. “When you’re dealing with custom-made clothes, there’s nothing you can’t do for a person,” he says. “You just need some time to do it.”
Italian craftsmanship is another common thread. “People traditionally think Florida is printed shirts and bright colors, with lots of white pants—that is not what our guy is looking for,” says Alexander, whose Hayes Haberdashery deals primarily in niche, high-craft labels, such as Isaia, Stile Latino and Manto Italia.
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Photography by Christina Bankson
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As a fourth-generation tailor, Aaron Gill understands the nuances of fit and fabric. At his Savile Row-inspired Downtown Fort Myers showroom, he educates clients on how to dress for style and comfort.
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Photography by Alex Crawford
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Arda Boyar—who opened Mondo Uomo at The Village on Venetian Bay in 1992—has watched that sensibility evolve over three decades. “We’re seeing maturity come in—and maturity, not by age terms, but distinction of quality,” he explains.
Unlike Palm Beach’s dandier register and Miami’s Latin swagger, the Gulf Coast gentleman remains restrained in his approach. Wardrobes lean into rich tonal colors, lightweight linen blends, and construction that feels more indulgent than it reads. Color and prints may be layered in subtly with knit polos or crewnecks.
Heat still dictates the wardrobe, but it no longer means lowering the bar. “I’ve been teaching guys that you don’t have to stop wearing a suit, you just need to wear suits that are specially made for this heat,” Aaron says. He turns them toward linen, bamboo and high-twist wool, and heat-proof construction, like unlined backs and minimal butterfly linings.
The style shift reveals something deeper about fashion: Tailoring is about building a look that moves the wearer through his day with ease. “This is the fun part of our store—the fun part of Naples—we don’t have a moniker that labels our fashion,” Arda says.
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Photography by Christina Bankson
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Gulf Coast style remains intentionally subdued in line with the laid-back lifestyle. At Tweeds in the Naples Design District, every detail of a suit, from color to materiality to construction, is chosen to move with the wearer from business to play.
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Photography by Christina Bankson
swfl menswear tweeds naples shop and showroom