Building on the success of his growing brand, Darian “Jack” Jackson plans to open two businesses May 15 in the same location Downtown.
Dapper D’s Cigars & Restaurant is at 11 N. Ocean St., adjacent to Cowford Chophouse, in the space formerly occupied by Island Girl Cigar Bar.
Customers enter Dapper D’s Cheesesteaks from the ground floor to choose among cheesesteak sandwiches, wings and fries. Or they can take a flight of stairs up to a separate entrance for Dapper D’s Cigars.
“I didn’t realize it, but literally, it’s two businesses opening at one time,” Jackson said.
Jackson needed the separate entrances to comply with state smoking restrictions. No smoking will be allowed downstairs in the restaurant, and no food will be served in the cigar bar.
Jackson said he is serving cheesesteaks because his favorite city is Philadelphia, where the sandwiches are a signature food. He is a Chicago native who became a Philadelphia Eagles fan during childhood.
“I grew up a Donovan McNabb fan. I hated the Bears growing up. So when he got drafted by the Eagles, I became a Eagles fan. I have immersed myself in Philly culture since I was a little boy, and now Philly is a city I can move around very easily.”
A 2025 Daily Record Entrepreneur of the Year, Jackson operates two other Dapper D’s cigar lounges, one at 725 Skymarks Drive in the River City Marketplace and one at 150 Fountains Way in The Fountains of St Johns. Neither serves food.
Jackson said he had looked for more than two years for a suitable location Downtown when Robert Feindt, owner of the former Island Girl Cigar Bar, called to see if Jackson would be interested in moving into the spot. Jackson bought the Island Girl business April 30, 2025, for $146,225.
In addition to Island Girl, the building, constructed in the early 1900s, formerly housed Downtown Cigar and Lit Lounge, two other cigar bars, Jackson said.
Jackson said he spent about $600,000 to refurbish the property inside and out. The contractor was Drako Construction Consulting, and the architect was JAA Architecture.
The Downtown Investment Authority awarded Jackson and building manager Austin Towery a $187,620 Food and Beverage Retail Enhancement Program Grant for the project. Towery also received a $29,952 DIA Facade Grant to improve the building’s exterior.
“When we took it over, it was in really bad shape. The outside facade was horrendous. The brick inside was falling apart,” Jackson said.
“We have a lot of old buildings around here. We took an old building and turned it into what you see today.”
Dapper D’s Cheesesteaks is about 2,100 square feet, and the cigar lounge is about 1,800 square feet.
Jackson plans to employ 25 people, he said.
The restaurant is fast-casual with 54 seats.
A 6-inch original cheesesteak costs $13, and a 12-inch is $18. Prices for a chicken cheesesteak are $11 and $15. The mushroom cheesesteak costs $14 and $19. All are topped with a choice of Cheez Whiz or ketchup.
Wings are $11 for six and $16 for 10, and are served with a selection of sauces.
The restaurant’s decor nods to Jackson’s love of Philadelphia sports.
Lito Sheppard, Brian Dawkins and Harold Carmichael, all Philadelphia Eagles players who attended William M. Raines High School in Jacksonville, are depicted in a mural painted on the dining room wall. Sheppard is scheduled to be at Dapper D’s grand opening at 11 a.m. May 15, Jackson said.
While he is an Eagles fan, Jackson is aware he is in the heart of Jacksonville Jaguars territory. A painting of a jaguar smoking a cigar is also part of the decor.
“I contemplated not putting anything Jaguars in here, but the stadium is a couple blocks away, and we have a good relationship with the Jaguars. Some of the Jaguars players frequent our lounges. With (Dapper D’s) being Downtown, we had to pay tribute,” he said.
The cigar lounge includes 24 leather lounge chairs and 13 bar seats. Both establishments serve a full liquor menu.
There also is a 250-square-foot walk-in humidor in the cigar bar.
Dapper D’s Cheesesteaks is open 11 a.m. to 10 p.m. Sunday through Wednesday and 11 a.m. to 11p.m. Thursday through Saturday.
Dapper D’s Cigars is open 10 a.m. to 11 p.m. Sunday through Wednesday and 10 a.m. to midnight Thursday though Saturday.
