Details:

John F. Kennedy personally owned gray felt Henry the Hatter fedora, custom made in Detroit and retaining its original black grosgrain ribbon. The interior sweatband is gold-stamped “JFK,” identifying the hat as having been specially produced for the President. The hat retains its original Henry the Hatter protective air-filled insert and is marked “Tilden Twenty” with a “Hand Re-Piped Edge,” reflecting the retailer’s premium custom construction.

This remarkable fedora was personally presented by President John F. Kennedy to his lifelong friend Benjamin A. Smith II, Kennedy’s Harvard roommate and one of his closest confidants. Smith remained an intimate member of Kennedy’s inner circle throughout his political career and, following Kennedy’s election to the presidency, was appointed by Massachusetts Governor Foster Furcolo to fill Kennedy’s vacant United States Senate seat. The present hat remained in the Smith family for decades before descending through the estate of Benjamin A. Smith II.

The hat also represents a fascinating artifact connected to one of the enduring myths surrounding John F. Kennedy. Kennedy is frequently credited with hastening the decline of men’s hat-wearing because he often appeared in public bareheaded, particularly during his presidency. While the popular story has become deeply ingrained in American culture, historians have shown that the decline of hats had begun well before Kennedy took office. His relationship with hats became so iconic that it inspired Neil Steinberg’s Hatless Jack: The President, the Fedora, and the Death of the Hat, which explores both Kennedy’s personal reluctance to wear hats publicly and the broader cultural shift that transformed American fashion during the early 1960s. Ironically, despite his “hatless” public image, Kennedy clearly owned and wore quality fedoras such as the present Henry the Hatter example.

Henry the Hatter of Detroit has long been regarded as one of America’s premier hatters, supplying custom hats to presidents, entertainers, industrialists, and public figures for well over a century. Custom examples bearing the wearer’s initials are exceptionally scarce, while those with direct presidential provenance are virtually unobtainable.

Fine condition overall, retaining an attractive shape with light expected wear from careful use. The interior gold stamping is crisp, and the original Henry the Hatter air-filled support insert accompanies the hat.

Provenance: From the estate of Benjamin A. Smith II, Harvard roommate and lifelong friend of President John F. Kennedy, former United States Senator from Massachusetts. Accompanied by a signed letter of provenance from Benjamin A. Smith III documenting direct family ownership.

Authentication:
Includes a full letter of authenticity from JG Autographs, Inc.

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Reference sku: 11691 1416399-1