A pair of Marc Jacobs shorts in crisp gray-and-white vertical stripes, cut high at the waist with front pleats and generously turned-up cuffs. Likely from Spring 2013, they recall the season’s graphic homage to 1960s Op Art, when Jacobs sent an almost dizzying array of stripes down the runway. Joanna bought them at Barneys and remembers wearing them “a lot” before eventually moving away from the shorter length. What she particularly loved was their ability to make shorts feel polished: “They were such great shorts—elegant at the same time.” And she had a firm styling rule: “I would never wear shorts with high heels. I’d wear them with flats or a platform.”

Marc Jacobs launched his namesake label in New York in 1984 and quickly became known for putting an irreverent spin on familiar American dress. His now-legendary 1992 grunge collection for Perry Ellis cemented his reputation for mixing high fashion with the everyday, an approach he continued with his own label. Over the decades, Jacobs has repeatedly played with prep, sportswear, vintage references, and ladylike dressing, often tweaking proportions or adding an unexpected detail.