Yale Club, ca. 1975.

The Old Yale Alumni Association of New York was founded in 1868 and was formalized as the Yale Club in 1897. An elite social club for alumni and faculty of Yale University, they moved into their current home at 50 Vanderbilt in 1915. Designed by Yale alumnus, James Gamble Rogers, the Renaissance Revival skyscraper was constructed on land leased by New York Central Railroad as part of the real estate development around Grand Central. The facade is rendered in limestone, brick, and terra cotta. The architect consulted with Warren & Wetmore, the architects of the Terminal and other nearby buildings, to ensure the club blended in with the style of its neighbors.

Supposedly (according to the Ken Burns documentary) the club horded enough liquor to last them through Prohibition. The club allowed female members beginning in 1968. To the scorn of some of the other clubs and the unhappiness of a portion of its members, the Yale Club became the first of New York's Ivy League clubs to allow a business casual dress code in 1999.