Neither piggy-shaped nor baked in a flaky crust, some say its resemblance to the British savory treat earned the Porkpie Hat its unusual name. Regardless, this flat-brimmed topper — and its kissing cousins — has gone from the chosen chapeau of boho artists (Charles Mingus made it the subject of his most famous song, ”Goodbye Pork Pie Hat”) to adorning the heads of some of Hollywood’s most dedicated lady trend-bots. Now that’s a hat trick.
Buster Keaton 1924
The silent film great, born of early 20th-century vaudeville, made the slim lid his signature.
Frank Sinatra 1950s
Oh, Sinatra, swinging cat of many hats. He wants to be a part of it, New Pork, New Pork!
Arsenio Hall 1986
On his talk show, he would go on to host cool daddy-o’s like Bill ”Sax Man” Clinton — hence the hep gear.
”Duckie” from Pretty in Pink 1986
So Jon Cryer didn’t get the girl. At least he had a hat to hold his tears.
Danny Wood, Jordan Knight, and Joey McIntyre of New Kids on the Block 1990s
Hangin’ tough, indeed! At the apex of their popularity, the New Kids wore hats like they were going out of style. Sadly, they did instead.
Johnny Depp 1993
His Keaton-esque turn in the mental-illness rom-com Benny & Joon included copping Buster’s look.
Jude Law 1999
Before Matt Damon’s talented Mr. Ripley bashed it in, Law’s head looked quite lovely covered up.
”Porkpie” from Sex and the City 2001
Carrie dated the manic jazzbo (Craig Bierko), to Big’s chagrin.
Tom Waits 2004
Perpetually cool: The bourbon-voiced singer and sometime actor’s trademark topper endures.
Sienna Miller 2006
The bestrawed starlet follows ex Jude and fellow Brits Pete Doherty and Kate Moss into the pork-y fray.
Though a crown seems more fitting for ”the Dutchess,” her brims runneth over — much like her humps.