Local Foodies Show You What To Wear To Chicago's Hottest Restos

A night out in Chicago can cover a lot of ground. We've got countless clubs, temples of mixology, and patios galore. But, a good time wouldn't be complete without a reservation at one of the hottest restaurants in town.
Today, we're talking to six fashionable locals who know a thing or two about dressing for Chicago's food-and-wine scene, because they do it all the time. Let these fierce foodies pick out your next to-die-for meal, and style you for it, too. That's right. Our experts are telling you all about their must-try city eateries and sharing the chic, seasonal dresses they'd wear to each. Now, all you have to focus on is what you'll order.
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Heather Sperling, Chicago Editor of Tasting Table

She recommends: Parker Long Pleated Dress. $286, available at Shopbop.

Why is this dress perfect for heading to a new restaurant in Chicago?
"I love Parker's breezy, patterned dresses. They can be dressed up or down, are incredibly comfortable, and can sustain being stuffed in an overpacked weekend bag. This one would work as well on a Randolph Street patio or as your farewell trip to Trotter's."

What would you wear with it?
"I'd wear a thick wooden bangle, a few simple gold chain necklaces, and some simple, strappy flat sandals. Or skip the necklace and bracelet and go for standout earrings."

Where do you love to shop in Chicago?
"I troll the Milwaukee and Damen stretch (Eskell, Tangerine, p.45, Intermix, Club Monaco), as well as Penelope's and Trillium on Division. I love a good session of dress-up at Barney's Co-Op, and have incredible stamina for Topshop and H&M forays."

What is your favorite summer dining spot right now?  
"I recently moved to Logan Square and cannot stay away from the patio and new bar room at Lula Cafe. After its renovation last fall, the food is more ambitious and creative than ever. My ideal night includes stinging nettle farfalle with halibut collar, green garlic and preserved lemon, and one-too-many glasses of rosé."


Photo: Courtesy of Heather Sperling
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Amanda Puck, of The Foodarazzi

She recommends: Helmut Lang HELMUT Kinetic Dress, $185, available at Net-A-Porter.

Why is this dress perfect for heading to a new restaurant in Chicago?
"I always love to get dressed for dinner. There is something so glamorous about the dining scene and reflects my roots from working in the business many years ago at Spago and in San Francisco. Going to a restaurant for me is also like going to an event."

What would you wear with it?
"Stacks of stone stretch bracelets with fireballs from space519, at least five or six of them. Or with my personalized monogrammed Moyna beaded camo clutch from space519, which I also wear with everything when I am hitting the town."

Where do you love to shop in Chicago?
"At space519 and Sarca, for fashion finds I don’t see anywhere else."

What is your favorite summer dining spot right now?  
"I would for sure rock this look at Balena; the décor is gorgeous. Their sophisticated cocktails and Chef Chris Pandel’s Italian menu are fun for me. And just wait until you try Amanda Rockman's Nougat desserts. But mostly, in the summer, you can catch me at the bar at Big Star."


Photo: CF Captured/Courtesy of Amanda Puck
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Audarshia Townsend, of 312 Dining Diva

She recommends: BCBG Max Azria Runway Brenda Colorblocked Dress, $458, available at BCBG.

Why is this dress perfect for heading to a new restaurant in Chicago?
"In the summer, I'm very active outside, resulting in a darker glow to my skin. The bright colors on these dresses POP against my tone. I love wearing dresses like these because they make a statement when you enter a room."

What would you wear with it?
"I'd wear them with strappy stiletto sandals (five inches!), a statement ring, and a clutch."

Where do you love to shop in Chicago?
"BCBG is my favorite store to shop for dresses, particularly because their styles fabulously complement my curvy, athletic frame. Additionally, I love the colors and styles of the dresses at any time of year."

What is your favorite summer dining spot right now? 
"I'm really feeling Farmhouse, in River North. It's unpretentious, yet lively and full of stylish and friendly folks. In addition, I'm obsessed with its gin-based cocktail menu, which is refreshing and ideal for dining and drinking alfresco."


Photo: Courtesy of Audarshia Townsend
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Carly Fisher, Food Writer & Editor

She recommends: River Island Tropical Body-Conscious Dress, $74.57, available at ASOS.

Why is this dress perfect for heading to a new restaurant in Chicago?
"I like this dress for a few reasons. First, it's a really loud print that demands constant attention. Therefore, it will most likely result in everyone telling me that I'm pretty all the time. Also, if you're like me and spill food on yourself constantly, then you can appreciate a pattern so distracting that it disguises unfortunate wine stains (guilty as charged!). Did I mention it's 100% cotton? If you're dining al fresco and it's a billion degrees outside, you'll thank me for not recommending a polyester-rayon blend.

What would you wear with it?
"To dress it up, I'd pair it with a chunky statement piece, some brightly colored heels, and a fresh flower holding together my 'do. To dress down, comfortable flats, a cardigan, and giant earrings — either gold hoops or some mismatched weird earrings randomly picked from the bottom of my junk drawer, like I do basically every day."

Where do you love to shop in Chicago?
"Target and TJ Maxx? If I had more expendable funds, I'd probably go to Penelope's and Una Mae's."

What is your favorite summer dining spot right now?
"Tacos are one of my favorite foods ever, so I've been crazy about Antique Taco lately. Also, I have to give big props to Nellcôte for having one of the most underrated brunches in Chicago right now. That pain perdu is sick, plus it's a massive space where I can coordinate a group outing effortlessly while in my morning fetal state."


Photo: Courtesy of Carly Fisher
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Kate Bernot, Copy Editor and Dining Reporter, RedEye Chicago

She recommends: AKIRA Colorblocked Loose Tank Dress, $39.90, available at AKIRA.

Why is this dress perfect for heading to a new restaurant in Chicago?
"Like 90% of American women this summer, I'm super into color. Greys and blacks are normally my 'color' palette, so I'm having a weird Pleasantville moment with my wardrobe this year. It's also crazy hot, so dresses should be loose (but not shapeless) to keep you cool as you're eating dinner, especially if you're on a patio. This dress is vibrant enough to make a statement, but because it's shift-like, it comes off effortless and easy. That's always smart."

What would you wear with it?
"The trick with vibrant dresses is not to be afraid of mixing colors, but to keep from looking like Rainbow-Brite. I'd grab a yellow patent-leather clutch, because I love yellow and fuchsia together; then keep small wedge heels neutral. I've also been pulling my hair back with headbands a lot this summer, mostly because I'm hot, but if you keep your hair sleek, it has a cool mod effect."

Where do you love to shop in Chicago?
"I was really upset to see that Fix in Fulton Market was closing (though I did take advantage of the resulting sale). Owners say they're not gone for good, so I'm hopeful. I also love to see the jewelry that new designers are bringing to Dose Market. When I can't make it to the monthly market, I like the edgy accessories at Wolfbait & B-Girls in Logan Square."

What is your favorite summer dining spot right now?
"Red Door, a new gastro-tavern that opened in the former Duchamp space on Damen, puts out some mighty fine food courtesy of chef Troy Graves. They have an underrated beer list, and oh yeah, arguably one of the best patios in the city."


Photo: Courtesy of Kate Bernot
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Kiki Luthringshausen, of Beauty And Her Feast

She recommends: Ali Ro Floral-Print Dress, $310, available at Cusp.

Why is this dress perfect for heading to a new restaurant in Chicago?
"As a food writer and a someone who is out at tastings and events several nights a week, my goal is to look nice, be comfortable, and wear something that will hide all those small plates I consume. Thus, I’m not a “skin tight” top-to-bottom girl. I have sins to hide. I also never wear white. I often eat standing at events and tend to spill. I prefer lightweight fabrics and look for a short dress that is cinched at the waste and blousy on top."

What would you wear with it?
"Fine foods and fabulous shoes ... my weaknesses. In summertime at events I’m in wedges. I also live for bracelets ... my arm farm. I buy them as I see them and wear them mismatched. I can’t help myself at the bracelet bar at space519 and Sarca. My staple is my turquoise Hermès, and I wear it even if it doesn’t match."

Where do you love to shop in Chicago?
"Saks Fifth Avenue shoe department, Intermix, Cusp, and Neimans. I don’t always have much time, so I need to go somewhere that carries a lot of different designers. It’s hard for me to justify an afternoon of strolling and shopping at smaller boutiques. Although I love it, I’m more of a turbo shopper."

What is your favorite summer dining spot right now?
"Tavernita and Barcito are fantastic for summer. GT Fish & Oyster is one of my favorites, and Giuseppe’s menu always makes for a good summer meal. And I can’t wait to try Trencherman."


Photo: Courtesy of Kiki Luthringhousen
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