REMEMBER PREP? That loud style of dressing that took the sportily cavalier look of WASPs to exaggerated, showboating levels? What Holden Caulfield might have, more succinctly, called “phony”?

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 tongue-in-cheek guide advised would-be preps how to pull off improbably layered oxford shirts, wide-wale corduroys and argyle socks. In prep’s heyday,...