Writer: Hailey Evans
Photos: Duane Tinkey
Think back to the last time you ordered a glass of wine. Did you rattle off your go-to favorite or peruse the wine list? Did your server offer pairing advice or tasting notes? Maybe you tried something new and surprised yourself by ordering the bold, juicy red instead of the crisp white.
If you’re like me, maybe you assumed a wine list was static, something the restaurant printed up when it opened and made available to everyone who walked in, as fixed as a soda fountain stocked with Coke or Pepsi products.
But I was wrong. Considering the passion and enthusiasm of restaurant staff across our city’s food scene, it should be unsurprising that wine lists are actually curated with just as much care as a chef’s seasonal menu. Owners, bar managers and sommeliers are constantly strategizing behind the scenes to build out a wine selection that can inspire, impress and evolve.
We spoke to three experts, each from a different type of establishment, about the process and philosophy behind their lists.
Cary Dascoli
Wine Director at Oak Park
Building the list
When Dascoli, a CMS Certified Sommelier, took over as Oak Park’s wine director in 2025, she inherited a wine list from Sam Tuttle, the wine director who helped open the restaurant and shape its overall tone. So there was already an esteemed wine list and an established precedent.
Bringing in new stock
Wine lists reflect the personalities who curate them, Dascoli said. As she spends more time in the role, she blends in her personal touches. “I love Beaujolais, so I’ve brought in more of those,” she said. But she also makes sure there’s plenty of diversity. “They should all have a purpose on this list. Are there options that pair with our variety of dishes? If a guest asks for something I don’t have, is there something close to their taste I can offer? I’m also a big fan of educating people who are curious to try new things.”
On the shelves
The Oak Park wine list currently boasts more than 1,000 labels, so guests are bound to find something they love.
Tasting notes
“Tasting comes in waves,” Dascoli said. When she sits down with representatives from different wineries or distributor companies, she’ll try a variety “to taste but also to learn the stories behind a brand or bottle and understand the value.” She’s built relationships over her years in the service industry and said having rapport with different reps helps her find the right things to add to the menu. When there’s a “hole” in the list — availability shifts due to grape health, vintage failure, export delays and tariffs — she works with reps to fill the gaps.
Nick Leo
Owner of The Cave
Building the list
Leo and his wife, Heather, opened The Cave in 2020 out of a personal passion for natural wine. Ever since, he’s been curating a wide variety of natural wines for retail and on-site consumption. “There’s not a hard and fast rule of what is or isn’t natural wine,” he said. Generally, he’s looking for wines that are organically farmed, fermented with native yeast and not subject to filtering, clarification or additives. “I don’t like to make qualitative statements that one kind of wine is better than another, but I’m just not interested in those kinds of [conventional] wines.”
Bringing in new stock
He likes to have diverse offerings and introduce customers to unknown or underrepresented wine regions or grape varietals. Just because he may not like something personally, he said, he will still bring it in if the wine is representative of the region. He started carrying Lebanese wine after meeting the winemaker and learning about the country’s 7,000-year history of wine production. Because he brings in wines from many different countries, he also considers the reputation of the importer and the kinds of wines they’re able to source.
On the shelves
Leo estimated The Cave has as many as 200 different wines available. “I try to fill the gaps, too. If there’s not a Cabernet Sauvignon here, what can do that instead?”
Tasting notes
Leo tries everything before he decides to bring it in. “Anything that’s not special order, I’m trying,” he said. He does tastings with his distributors two to three times per week, especially making sure the wine in a shipment is still good. Natural wine is “a living thing,” he explained, and because of the natural fermentation and absence of stabilizers or preservatives, “some wines ‘die’ three hours after opening. I try not to push bottles too long.” When he travels to wine fairs or conventions, he’ll often try hundreds of different wines looking for new or interesting bottles to bring in. Once, during a conference in L.A., he tried about 300 in one day.
C.J. Bienert
Owner of The Cheese Shop
Building the list
Like The Cave, The Cheese Shop does a lot of retail sales, but Bienert doesn’t focus solely on natural wine. When the shop first opened 15 years ago, he was bringing in Beaujolais crus and “other stuff nobody really cared or knew about,” he said. Since then, he’s tried to keep the list refined but approachable and competitive. “Retail competes with the internet, where you can go to any online store or even a bigger warehouse and make your purchase,” he said. Part of what sets The Cheese Shop apart, he added, is that it doesn’t charge a corkage fee so guests can come in, select their bottle and enjoy it right there.
Bringing in new stock
“We buy wine from people, not corporations,” he said. His friendship with a rep from Iowa wine distributor Meadowlark Wines, for example, helps him discover new standouts. He’s also been getting into draft wine and now offers up to eight wines on tap at The Cheese Shop. “We always have a special wine by the glass, that’s where we can try out weird stuff,” and decide what to keep based on customer feedback. He also checks to be sure the list covers the basics — full-bodied reds, crisp whites, sweet and dry. “I’ll carry a Malbec because I know people want it, but I’ll work with my distributor to find a cool one.”
On the shelves
The Cheese Shop has several hundred bottles stored in the basement cellar. “More than we need,” joked Bienert.
Tasting notes
Bienert tastes an average of five wines per day and sometimes brings in new wines each week. “Wine is an agricultural product. It changes with the seasons, so it makes sense to change with it,” he said. He hopes Iowa will expand its self-distribution laws, which would allow him to bring in even more options from wineries in other states.
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