New Era 59Fifty Covid Mask Pittsburgh Pirates Fitted Hat

The Jolly Roger never looked this timely. This New Era 59Fifty wears a vivid scarlet crown paired with a deep purple visor — a two-tone that has nothing to do with Pittsburgh's standard black and gold, and everything to do with making a statement. The under brim reveals gold, with navy piping along the brim edge tying the whole palette together. Up front, the classic Pirates skull-and-crossbats mascot has been redrawn for a specific moment in time: the Bucco is rocking a red paisley bandana pulled up over his face — a dead-accurate portrait of 2020 streetwear dress code. The embroidery is dense and detailed, white-bordered with purple and lavender thread that pops hard against the red wool. On the left side sits a circular "Est. Pirates" commemorative patch in cream and navy, centered on a pennant flag bearing the "P" — a nod to the franchise's deep roots. The gold under brim with a baseball-stitched center tack completes the build.

A lot of hats claim to be collectible. This one earned it. The bandana mask on the Jolly Roger is a freeze-frame of 2020 — every walk to the bodega, every outdoor fit, every fit pic with the face covered. Some brands tried to capitalize on the moment with half-measures. This hat made it permanent, stitched into the logo itself. That's the difference between a novelty and an artifact. Ten years from now someone's going to pull this out of a box and immediately know exactly when it was made, the same way a "Y2K" tag or a "September 11" flag pin instantly places you in time. You don't find pieces like this — you hold onto them.

How to Wear It

The Streetwear Edit
Lean into the two-tone hard. A washed burgundy or brick-red heavyweight crewneck, relaxed-fit black cargo pants, and Nike Air Max 95s in the "Neon" or "Total Crimson" colorway — the chunky silhouette matches the hat's energy without competing with it. Keep accessories minimal: a simple chain, nothing flashy. The hat is the conversation piece.

Her Way
Style it as the anchor of a tonal red moment: a fitted red moto jacket over a black bodysuit, straight-leg black trousers, and patent or matte black chunky loafers or platform sneakers. The gold under brim peeks through and adds warmth. Small gold hoops, clean nails. This hat looks intentional on a woman who knows exactly what she's doing.

The Archives
Treat it like what it is — a document. Keep the surrounding fit clean and era-neutral so nothing dates the look except the hat: raw-hem dark indigo jeans, a plain black or white tee, and black low-top Air Force 1s. No graphics, no logos. Let the Jolly Roger in the bandana do all the talking. This is a museum piece. Wear it like one.

Explore more iconic fits at 402fitted and dive deeper into fitted hat culture on our Cap Chronicles blog.