On a crisp Thursday in Chicago, she reached for her olive green chinos and the ivory sweatshirt with chocolate brown piping—equal parts comfy and pulled together—perfect for a morning spent building block towers and reading the same picture book three times in a row. Little Book Club had to be canceled (curse the season of sniffles), so she and her toddler made their own fun at home, dancing in pajamas and nibbling on mid-morning bagels. Her white leather sneakers and go-to gold hoops added just the right amount of polish, especially since she and her husband were trading sippy cups for champagne flutes later—boarding a flight to Boston for a wedding weekend that promised just the kind of romance and room service every city mom dreams of. LTKTravel LTKWorkwear LTKStyleTip