In the late 1970s and early ’80s this overcooked iteration of the real deal kicked off a broader fashion trend, as dissected in the 1980 best-seller “The Official Preppy Handbook.” That ...

See the menswear pieces we loved from the Fall/Winter 2026 shows at Milan Fashion Week, featuring Ralph Lauren, Prada and ...

Whether or not you lived through it, there’s no denying that nostalgia for the ’90s and early 2000s has been dominating the runways lately. To the shock of many millennials, polarizing pieces like low ...

He’s become the collaborator of choice for heritage brands such as J. Crew and Sperry that are trying to reach a customer who’s no longer impressed with the preppy lifestyle and entranced with ...

Massimo Giorgetti’s antidote to the world’s noise is focusing on clarity in design, evolving his preppy fashion with textures and an evocative addition to his signature mottos.

Preppy fashion goes back to the ’40s. It had its origins on Ivy League campuses among sporty men who played tennis, rugby, who sailed, hunted or rode horses. In the early days, Brooks Brothers was the ...

FOR A FEW YEARS NOW, menswear designers have been tapping the well of classic prep, and this spring, labels like Thom Browne, Band of Outsiders, Shipley & Halmos and Asos are exploring its quirkiest ...