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Dressing for Success: H. Craig DeLongy’s Journey to High-End Fashion

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Story by: Emily Baker and Jim Carchidi

John Craig Clothier has been a men’s fashion icon since first opening on Park Avenue in 1996. The flagship location set a standard for selection and customer service and stands as a testament to the vision of owner, H. Craig DeLongy.

From his early retail career to his recent title of MR Magazine’s Merchant of the Year, DeLongy’s journey carries a narrative of passion and community spirit. The John Craig brand has continued to expand throughout the state with its eighth shop recently opening in Ocala.

DeLongy developed an understanding of market trends and consumer behavior as a founding member of Champs Sports. “In 1974 I was a golf pro in Missouri and was in Florida to play in the winter tours,” he said. “I had been doing that for a few years and decided it was time to settle down and get a job.”

H. Craig DeLongy’s career as a golf pro launched a pivot to retail fashion that landed on Park Avenue.

On the recommendation of a cousin, who was one of Champs Sports’ two founders, DeLongy joined the West Bradenton-based sports apparel company and eventually became a partner in 10 locations. Oddly enough, his true calling in men’s fashion retail was also a product of his love of golf.

“During a round of golf at Interlachen Country Club, a conversation about aspirations led to my realization,” he told the32789. “I wanted to create an upscale men’s store; a place that offered more than just merchandise, but also an experience.”

Beyond offering upscale inventory, his ideal shop filled a void of personalized service with standards that inspired customer loyalty. “It was about building a community,” he said and further elaborated, “a place where fashion is about the people as much as the style.”

The company flagship location was chosen for convenience and evolved into a local icon.

To that end, DeLongy set about identifying the proper market and building a brand that reflected and adapted to the needs of its customer base. Being a Winter Park resident – his home is just .75 miles from Park Avenue – the ideal location was easy to find. Originally a sublease space attached to a neighboring gift-shop, he describes the first storefront as a leap of faith that became a labor of love.

“Our way of doing things has always been about more than just selling clothes,” he said. “It’s about crafting an experience, making sure each person who walks into our stores feels like they’re part of something bigger.” DeLongy sees each location as an extension of its community. “We dive in deep; getting to know the people, the vibe. That’s our secret sauce, being right there in the thick of it all with our customers.”

About 27 years after breaking into the Winter Park market, and 14 years after launching the neighboring Current by John Craig luxury boutique, Craig is ringing in 2024 with eight locations: the most recent situated in the Equestrian Hotel, 8510 NW 17th Lane in Ocala, and part of the 11,000-acre World Equestrian Center (WEC), adjacent to Golden Ocala Golf and Equestrian Club.

“Ocala caught our eye with its lively atmosphere surrounding the World Equestrian Center,” he said, pointing out its unique vibe that is complemented by floor-to-ceiling windows providing ample natural light throughout the shop.

The 1,600-square-foot store offers the same friendly and professional service found in the other locations but also features luxury design touches like handmade cabinetry. The (WEC) is also the only John Craig store carrying Ralph Lauren in addition to mainstay brands like Canali, Castangia, Peter Millar, Waterville, Di Bianco and Samuelsohn. Custom shirts and suiting are also available.

“The WEC brings to town the same customer that we serve in all of our other locations,” said DeLongy. “We are filling a niche in Ocala that was previously underserved.”

His pride in the new location is outmatched by the pride he feels in his staff. DeLongy’s appreciation for his team is clear and heartfelt. “Our crew is everything. We’ve got a low turnover rate because we’re like a family. These folks, they’re the heart and soul of John Craig. Without them, we’re just another store.”

Reflecting on his career, DeLongy sees the bigger picture. “It’s about building something that lasts; a legacy where style, business, and community all come together,” he said. “John Craig is a place where our customers become our friends and part of our extended family. That feeling – that connection – that’s why people keep coming back. It’s what’s made us who we are today.”

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