Justin Timberlake in a Fedora Photo 35

Photo 35 from Justin Timberlake in a Fedora
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50 Most Legendary Hats Throughout History Justin Timberlake in a Fedora

Justin Timberlake in a Fedora

Timberlake, natty man that he is, loves himself a fedora. Over the years, the Timberlake hat has transformed its look and feel — from the early Sherlock Holmes–like cap of his ’N Sync years (at left) to an unstructured (mohair) bucket hat to, more recently, an onslaught of black porkpies — accessorized, of course, with a jaunty red feather.

Photo:
Jeffrey Mayer/Getty Images