When he was 19, Guido Conti Caponi spent his gap year working for Loretta Caponi, the Florentine linen bottega, or atelier, founded by his grandmother in 1967. His mother, Lucia, started working for the business around the same age, helping Loretta sell tablecloths, sheets, and charmingly fusty smocked nightgowns to European aristocracy from the same storefront they still inhabit today on Via delle Belle Donne (literally, “Street of the beautiful women”), a few steps away from the city’s Santa Maria Novella basilica. “I didn’t want to study, so I was really determined to work for the business,” Guido recalls. “But then after one year—and they were right, by the way—my mother and grandmother told me to take a degree first, and then I could come back.”

Same but different: Caponi released a ready-to-wear line of its signature nightgown dresses (left) while its homeware products remain custom.

So he went to Milan, where he noticed chic twentysomethings wearing the Caponi blousy floral nightgowns as dresses, belted at the waist, ruched collars stretched down off their shoulders, and paired with heeled boots. They had always been a best-seller, but a new generation of women were putting their own spin on the family classic. It seemed like a missed opportunity. “Our marketing tool was only word of mouth, which still is the best one, I think. But it was not enough,” he says.