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.

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.

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Photos by Hailey Bollinger
Oakley Wines is a cozy spot off of Madison Avenue’s main drag with an upper-level wine bar and lower-level Cellar speakeasy-style space with live music. Hailey Bollinger
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. One of their first missions was to expand the menu to include more seasonal dishes. Hailey Bollinger
Customers love chef Lydia Jackman’s Tomato Pie. “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,” Jackman says. Hailey Bollinger
The upstairs wine bar Hailey Bollinger
Oyster mushroom toast. “The mushroom toast is so good, it has so much umami, so meaty and filling and savory,” says owner Stephanie Webster. “It’s like you’d think there was meat, but it’s vegan.” Hailey Bollinger
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. Hailey Bollinger
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. Hailey Bollinger
Mussels and toast Hailey Bollinger
The Cellar downstairs offers a a low-lit speakeasy-style space with room for live music. Hailey Bollinger
Charcuterie board Hailey Bollinger
Hailey Bollinger
Pork rillette Hailey Bollinger
Fonduta Hailey Bollinger
Hailey Bollinger
Wall of wine Hailey Bollinger
Liquor available in The Cellar Hailey Bollinger
Hailey Bollinger
Hailey Bollinger
Hailey Bollinger
Cheese from The Rhined available at Oakley Wines Hailey Bollinger