Riiminka Design's Red Skull Shirt and Black Skull Jeans - $45 each

Experienced scalawags will take the breathability and durability of rough cotton over that flimsy, flame-retardant crap from Party City any day. The jeans feature a rugged construction well-suited to on-your-knees deck swabbing and a patch pocket roomy enough to conceal a spider monkey. The Spice Islands palette on the unisex blouse guarantee you'll stand out in even the thickest cinematic fog, though the Chief Laundry Officer may want reminding of the fate awaiting those who dare toss that shirt in the whites.

826 Valencia's Pirate Supply Store Flags - $11-$22

There's no harm in pledging your allegiance to Edwin Teach, Bartholomew Roberts or Christopher Moody when every Pirate Supply purchase, from glass eyes to the aforementioned icons' skeleton-centric personal flags, supports free creative writing workshops and the drop-in tutoring center in this worthy venture's stern. (Should your sloop weigh anchor in San Francisco, drop by the Pirate Supply Store to take some lard from the in-house barrel, accompanied by a parchment detailing the top ten uses for lard.)

Pirate Adhesive Bandages - $5 a box

Handy for any injury that doesn't require a hook or a glass eye! Store your plunder in the old-school metal box!

Captain Bogg & Salty, Pegleg Tango - $15

With a style more Feathersword than fierce, Captain Bogg's Pollywog crew may drive older listeners to the brink of mutiny, but the thematic passion that leads them to perform in pirate drag is difficult for any to resist (let alone the mothers of Portland, Oregon, who reportedly have a lot of raunchy fun discussing which of these toddler-friendly seamen would be most welcome below decks). While the intentionally silly lyrics of such pop-inflected ditties as "Pirate Party" tend to bring out the cold fish in me, the waist-high crowd gives them a rollicking yo-ho-ho. The wistful "What It's Really Like on a Ship," on the other hand, will cause many a barnacled old seadog to blubber like a sentimental landlubber.