Most teams wear a hat. The late-’70s Pittsburgh Pirates wore a declaration.
The pillbox cap—flat-topped, striped, and cocky as hell—looked like something a 19th-century train conductor might’ve worn after three shots of Wild Turkey. And the Buccos didn’t just bring it back… they owned it.
Revived in 1976 as a throwback to baseball’s early days, the Pirates’ pillbox hat turned heads, raised eyebrows, and clashed spectacularly with every uniform in sight. Three golden stripes wrapped around a stiff crown that looked like it could deflect foul balls—and probably did. Add in those mustard-colored jerseys and pajama-bottom pants, and you had a team that looked like it had been sponsored by Crayola.
But man, they made it work.
Willie Stargell turned that hat into a crown. He dished out embroidered stars for great plays, slapping them on his teammates’ lids until they looked like Little League generals. Dave Parker wore his tilted like a jazz saxophonist who could also hit .300 and throw out runners from deep space. Even the pitchers wore them with pride—despite the aerodynamic disadvantages of a hat shaped like a drum lid.
Was it practical? Of course not. Was it iconic? You bet your polyester double-knit pants it was.
No one else in the league could’ve pulled it off. But the Pirates didn’t want to blend in—they wanted to swagger, to swing hard, and to look like a gang of turn-of-the-century saloon bouncers who accidentally won a World Series in 1979.
The pillbox was a fashion risk that paid off in full. It said:
“We’re here to win, and we’re going to look like absolute maniacs doing it.”
And honestly? We’ve been trying to recapture that energy ever since.
