the society man an analysis of the old

Money Style

by sean toomey

From the days of the broad-shouldered financiers who peddled an English drape to the dependable flannels of the power suit, Ivy League campuses have always been hotbeds of the styles associated with the upper class. Originating in Princeton and Yale (sorry guys—we can’t take credit for this one), high society fashion has managed to sneak its way into every decade since the height of its popularity in the ‘50s and ‘60s. Somehow, we forget all about it just in time for the next Nantucket Red-clad man to start the whole damn cycle over again. Here I will be focusing on the newest iteration of the preppy look—the old money style.

Its legacy originates in the collegiate look of the 1930s, which evolved into the Ivy look of the ‘50s and ‘60s. Ralph Lauren carried the style in the ‘80s into the business casual look of the nineties. Think navy blazers with gold buttons, cricket sweaters, gray flannel trousers, Oxford shirting with button down collars, bass weejun penny loafers, and lots and lots of tweed—all of which are style points that have been consistent in every decade of the style.

Even with this legacy, now is a strange time for prep to reemerge. ...