Okay, not a hat song per se, but what’s the first thing that Ira Gershwin lists in his litany of memories of a lost love? What else but, “The way you wear your hat…” Fred Astaire recorded it first (1937) Francis Albert (that’s Mr Sinatra, to you) had a tilt at it in ’62, but we remain hypnotised by the Billie Holiday version.
You Can Leave Your Hat On (1997)
For so long associated with knickers, Sir Tom Jones turns his hand to hats here, suggesting to his companion that she divest herself of all items of apparel, while granting her leave to keep her titfer firmly in place. The old dog twinkles so playfully in his take on Randy Newman’s number that it’s impossible not to laugh out loud.
Easter Parade (1933)
By the immortal Irving Berlin. “I could write a sonnet/About your Easter bonnet.” Sheer lyrical class.
Wherever I Lay My Hat (That’s My Home) (1962)
Written by Barrett Strong, Norman Whitfield and Marvin Gaye, and recorded by the latter in 1962, this remains a soul classic despite having been assaulted by every clapped-out, pasty-faced crooner and karaoke bum from here to Blackpool. A testament to a great song.
Leopard Skin Pillbox Hat (1966)
Dylan’s obscurely hilarious attack on a hapless victim of fashion. Of all the ink that’s been spilled analyzing Dylan’s 50 year career, precious little of it has been dedicated to his hats. Yet from toppers to caps to wide-brimmed fedoras, he remains the greatest hat wearer of the rock age. The key to his success? Simple: wear the hat, don’t let the hat wear you.