Sting, however, received a more welcome reception when he popped up in party photos from a Norman Lear book bash in New York a few weeks ago wearing a form-fitting black puffer vest under a gray tweed suit — indoors, red wine in hand. “Once you get over the initial shock of this particular juxtaposition, it doesn’t look half bad,” The New York Observer wrote.

While the puffer-vest-as-fashion-item still can furrow brows in the mainstream, it’s a look that has been building for years among the cognoscenti.

Europe, where chic (and pricey) Moncler down vests have long been part of the Gstaad après-ski uniform for the style crowd, has been a big influence. Italian men in particular took to wearing puffer vests over custom suits as armor against the crisp-but-not-freezing winter evenings when tooling around, say, Rome on their Vespas and Ducatis, Mr. Kalenderian said. Before long, a look born of motor sports practicality morphed into a style trend.

On these shores, the retro-Americana revival of recent years also fueled interest in classic technical clothing, said Jesse Thorn, the NPR host and men’s wear blogger who runs the site Put This On, as bearded young tastemakers developed a new appreciation for rugged outdoors apparel, including vests, from heritage brands like Crescent Down Works and L.L. Bean.