Soon after the British painter known as Gluck, née Hannah Gluckstein, debuted her first solo show at London’s Dorien Leigh Galleries in 1924, her signature men’s wear attire, which included tailored shirts from Jermyn Street, caused such an uproar in the press that she felt compelled to issue a statement: “I just don’t like women’s clothes,” she said. “I believe the time will come when … in the matter of dress, the girl of the future will be indistinguishable from her brother or boyfriend.”

While her prediction hasn’t proven entirely true, button-up shirts like the ones Gluck favored have indeed become a classic — rather than convention-defying — component of women’s wardrobes, thanks partly to postwar fashion icons like the actresses Marlene Dietrich and Katharine Hepburn. And yet a wealth of contemporary designers, from Rachel Scott of the New York-based brand Diotima to Olivia Villanti of Mexico City’s Chava, are proving that the garment is still ripe for reinterpretation.

“I love reshaping classics with a precise eye for detail,” says the Dutch designer Flòrian van Zuilen, 32, who launched her Amsterdam-based brand, Flore Flore, in 2021 with organic cotton T-shirts. Last week, she debuted a five-piece collection of white button-ups that she spent a year and a half perfecting. Ranging from slim-lined to oversize, the shirts are handmade in Portugal and finished with carefully researched details. The pronounced collar on the Giulia, for example, takes its cues from vintage Armani. And like van Zuillen’s tanks and tees, the shirts will eventually be offered in a host of colors. As she says, “There’s not just one perfect shirt.”

The New York-based designer Nili Lotan, 66, agrees. Since founding her label more than two decades ago, she’s introduced a new iteration — be it striped or solid, shrunken or relaxed — every season. “When a woman walks into the room, you want to be impressed by her, not by what she’s wearing,” she says. “The button-down is nothing loud, but it brings one’s natural beauty out.” Below, a few of T’s favorites.