Event planner Tom Kehoe of Kehoe Designs said that when the Women’s Board asked him to execute the event, they wanted the look to be “elegant, but with a definite ‘wow’ factor.” Kehoe transformed the ornate ballroom by bringing in edgier elements, starting with black-painted mannequins that stood on elevated platforms and wore skintight dresses accessorized with custom-designed hats. “We felt this added a touch of fun and drama, something every woman loves,” said Kehoe. One hat featured a 3-D Eiffel Tower, another was adorned with 175 butterflies, and still others were trimmed with feathers, tulle, faux oranges, lace, and more.

Elsewhere in the room, a cerise-and-black color scheme included pink roses in floral arrangements at the entryway and on tables, hot pink uplighting on the walls and buffets, and linens of black lamour with cerise organza overlays. Blue Plate catered the cocktail party, and guests roamed the room, sampling from a macaroni-and-cheese tasting station, an Asian buffet, and a cupcake-laden dessert table.

The 90-minute fashion show was a study in organization, with the models—among them women from Chicago’s philanthropic families, media personalities, doctors from Rush University Medical Center, and children on scooters and skateboards—proceeding across the stage in practiced formations, directed by the show’s mastermind, Skip Grisham. Allan Kaye and the Incognito Orchestra played backup to the procession, with additional vocals provided by Anne and Liz Callaway, sisters and singer/songwriters who do an act called “Sibling Revelry.” Local newscaster Mary Ann Childers announced each of the 19 segments, which featured participating retail stores such as Saks Fifth Avenue and Macy’s and local boutiques Jake and Neapolitan.