At 40, J. Crew Shakes Off a Midlife Crisis

Twenty-two stories above the palm-tree-studded court of the Brookfield Place mall in Battery Park City, the J. Crew men’s wear designer Brendon Babenzien was dressed for work on a sunny October morning in a chambray shirt and jeans, topped by a Shetland wood cardigan.

Bedecked with rows of pastel pink roses, blue daisies and purple irises, this tea cozy of a garment would have looked at home on Mrs. Doubtfire. On a founding father of fashion’s streetwear era — who, it’s worth noting, designed the sweater not for his day job at J. Crew, but rather for his own label, Noah — it read as intended: ironic, a little subversive. Very secure in its coolness.

This was a garment that, in many ways, the retailer Arthur Cinader could never have prognosticated back in 1983 when he founded J. Crew. At the dawn of the preppy era, Mr. Cinader named his mail order business after an Ivy League sport and slapped the initial “J” in front to conjure the illusion of provenance.

In the 40 years since, the preppy aesthetic Mr. Cinader wanted to mass-market has been rejected and embraced, defined and redefined so many times that today, a Nirvana T-shirt has apparently entered the Gen Z notion of “how preppies dress.” Along with it, whatever constitutes “American style,” and the whims of the American consumer have zigged and zagged, and the company Mr. Cinader started has striven — sometimes with great success — to keep up.