It’s a bright Friday in August, and the city mom is effortlessly chic in blue linen shorts and a green-and-navy striped tee, the kind of outfit that feels as breezy as the morning itself. Brown sandals keep her grounded between poses, while her go-to gold hoops, layered herringbone and graduated rope necklaces, and her new stack of permanent bracelets—topped with a diamond tennis bracelet—add just the right touch of sparkle as she moves through the day. The morning flies by at a photoshoot in preparation for The Chicago Literary Salon, made all the more fun by the photographer and her former-student-turned-friend, whose laughter and encouragement bring her vision vividly to life. Now, with her shots wrapped and her excitement buzzing, she’s ready to pick up her son from daycare and kick off a weekend filled with airplane acrobatics and waterfront fun at the Air and Water Show, all while feeling completely herself in her signature mix of comfort and cool. LTKWorkwear LTKShoeCrush LTKStyleTip