Page Six is reporting that a disturbing tragedy has befallen one of New York City’s most hallowed institutions: Yale Club members are not following the dress code.

In advance of Wednesday’s annual meeting an unnamed member wrote to leadership that the club was failing to uphold its standards for excellence in dress and behavior, the gossip column gleefully reported. The failure to uphold dress standards has led, the member wrote, to a “sad decline in the atmosphere and spirit of the club.” He offered an example in which “a young man (a Yale law student) was wearing a tee shirt emblazoned in large letters with: ‘F—ck Forever.’” (As the Ivy League feeds on notions like heritage and legacy and tradition, the offense is understandable.)

Yale’s dress code is pretty standard fare for the New York City private club scene: “business casual”—a concept as elusive as the Ivy League admissions process—and a byzantine maze of rules about where jeans can and cannot be worn, followed by a call for “neat, respectful appearance.”

But among its starchy Midtown neighbors, the Yale Club has a history of innovative leadership in the face of changing attitudes in dress. In 1999, The New York Times reported on the club’s relaxed dress code: “MORAL CRISIS: YALE CLUB GOES CASUAL ON FRIDAYS,” the headline read. The board had just voted to allow polo shirts, sneakers, jeans, and khakis—a decision met with a bite worthy of the school mascot, the bulldog Handsome Dan (who, it should be mentioned, usually appears nude).

The Yale Club's then president's explanation was strangely foretelling: “We need to engage the interest of more and more younger members, professional people who are not just lawyers and accountants but also architects and people who work on the Web." Can't you just picture the cigar smoke that appears when he asks you to connect on LinkedIn?

The Harvard Club, on the other hand, insisted on enforcing the standard coat and tie: “I wouldn’t expect the rowdies from New Haven to understand.”

But eventually, it followed in Yale's footsteps, and now allows “business casual” in much of the clubhouse, though this being Harvard—which the U.S. News & World Report ranked No. 2—and not Yale—which the U.S. News and World Report ranked No. 3—the Harvard Club actually defines what that means.

The Yale Club now finds itself back at this same impasse: How will it draw its monied, younger alumni away from glossier alternatives like the Soho House, where suits are infamously banned? As logo T-shirts, flip-flops, and sweatshirts define the uniform of today’s tech-based billionaires, Yale must ask itself: Do we want to dress for world domination, or just dinner at the Tap Room?