What to Wear to a Gala-Boys & Girls Club Of Chicago Summer Ball

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The spring/summer gala season in Chicago rolls on and next month one of the city’s long running iconic galas will welcome some of Chicago’s top power players from the corporate, civic and philanthropic world. We’re talking about the 77th Annual Summer Ball hosted by the Women’s Board of Boys & Girls Club of Chicago co-chaired by Andrea Chadwick and Whitney Huffsmith.

If the scene from last year’s gala, co-chaired by Kate Melman and Kelly Rosen Lagrange is any indication, its looking to be another fab record setting evening.

This year, the event moves to Theatre on The Lake and if you’re attending adhering to the dress code, you want to show up and show out in a show stopping outfit. The team at SociaLifeChicago fashion ourselves as your go to lifestyle curator private concierge so we’ve done the heavy lifting combing through racks and fashion sites to curate 16 stunning gala dresses guaranteed to land you on the evening’s best-dressed on the scene list while supporting an incredible cause for Chicago’s youth.

From sculptural architectural gowns like this MacDuggal number to fluid, sunset-inspired silks like this Katie May Bita gown, we’ve selected dresses that you can shop or serve as inspiration. There will be a slew of things that may require your attention before the gala, finding a beautiful dress to wear to Summer Ball 2026 shouldn’t be one of them. Scroll down through to find 16 show-stopping dresses that commands the room; save your favorite look for your fitting, and share this with the group chat! You can shop the whole collection on ShopMY.

Elie Saab Off-The-Shoulder Silk Double Georgette Gown | SHOP