Oakley Wines is a cozy spot off of Madison Avenue’s main drag. The upper floor wine bar and bottle shop is minimal, bright and full of grab-and-go selections, and an unassuming staircase leads down to The Cellar, a low-lit speakeasy-style space with room for live music.
Oakley Wines changed ownership last year when Stephanie and Dave Webster, who also own The Rhined cheese shop in OTR, were ready to expand their brand. They opened The Rhined in 2017 and acquired Oakley Wines in September 2018.
“I had just gotten back from France for a month, and it was the first time I’d left The Rhined for that long,” Stephanie says. “When I got back, everything was under control, and I thought, ‘Maybe now would be a good time to do a second thing.’ A friend of mine reached out and said, ‘I know someone who is selling his business in Oakley, I think you’d be a really great fit.’”
The Websters already held various wine- and cheese-related events at their shop near Findlay Market, and the opportunity to expand had appeal. Oakley Wines had featured a small plates menu since before the ownership change but putting food front-and-center at the wine bar was one of the Websters’ new priorities.
“Coming from the cheese shop, the cheese is so much our brand and what we do, so we wanted to get really great cheese and to be proud of the food we can serve here,” Stephanie says.
Oakley Wines’ chef, Lydia Jackman, moved to Cincinnati from Nashville after working in restaurants with a focus on seasonal foods. She began bartending and serving wine part-time at Oakley Wines to learn more. With her experience, the Websters asked her to craft a new menu that would be delicious and fairly uncomplicated, given the small downstairs kitchen at the wine shop.
“We wanted to use local produce, plate things beautifully, and still make it fairly easy to create,” Jackman says.
As the Websters accustomed themselves to the strategy needed to run a two-location business, they realized that an executive chef over the events and food at both The Rhined and Oakley Wines made sense. Jackman ended up accepting the job, and she has brought her own Southern and seasonal twist to the food offerings, from the day-to-day menus to the catering options for private parties.
“My direction is definitely creating a multi-cultural experience where you can eat French, Italian and German-inspired dishes with our by-the-glass or from-the-bottle wine list,” she says.
While there are certainly hearty items on the menu at any given time, Jackman tried to think about the breadth of options she wanted to include, as well as the regulars she already knew from bartending.
“Most people come here to get a glass of wine and a snack,” she says. “Our regulars know this is a place to come for food, and we can accommodate dietary needs. A really cool thing about being a bartender first before becoming the chef is that I know a lot of people that come in, and I can arrange something for them that makes them comfortable. Every time I walk upstairs, there’s someone I know. It’s about getting to know people and caring for them.”
Stephanie has a few favorites despite discovering constant novelty in Jackman’s cooking. “The mushroom toast is so good, it has so much umami, so meaty and filling and savory,” she says. “It’s like you’d think there was meat, but it’s vegan.”
Another crowd pleaser — the tomato pie — has its roots in a cooking rivalry between Jackman and her sister.
“We have little cook-offs when we go home. I make dinner one night; she makes dinner another night. We have a big family and we decide who does each dish better,” she says. “Tomato pie is in a pie crust, either pastry or cracker. I use a water buffalo cheese from The Rhined, then I dredge the tomatoes in corn starch and add spices, as well as creating a caper aioli on the side.”
Stephanie adds, “She uses heirloom local tomatoes, alternating yellow and red, so it’s also just beautiful. Every time she makes it, everyone in the bar says, ‘What is she making?’ because it smells so good and smells the whole place up — they are ready for a slice of tomato pie as soon as it comes out.”
As the Oakley Wines menu grows and their expansion comes into full fruition, they also hope to host local chef pop-ups and evening events that feature both wine and food. (They’ve already had several.)
“We’re looking forward to the winter; it’s really busy because of the fireplace downstairs, so I’m sure we’ll have a good, hearty winter menu,” Stephanie says. “We’ll continue to see Lydia grow in ways she wants to, sourcing great ingredients, and tying both of our businesses together over the next year so that these two places are synonymous in quality.”
Oakley Wines is located at 4011 Allston St., Oakley, oakleywines.com.