like this:
Pirates always wear sparkles.
...well, to formal events anyway.
_____
Edit: Spoilered v1.5 events for our eager mobile users awaiting the almost-here update
OK okok. Emily seems a good choice for a Pirate theme, with her taste for color and general knowledge of Tailoring.
Yeah parrot, whatever, go for the obvious why don't you...
Choose the Skull Shirt or Red Striped Shirt at character creation, either can be Tailored later on so you have both. There's also the dyeable Dark Striped Shirt you can Tailor from a Tigerseye later on (and Omni Shirt, just sayin'...). Probably dark brown pants to start?
Pirate Hat early on
but grind for the Deluxe Pirate Hat so you can get the eyepatch and tufty frilly bit modeled above by our heroine. The Pirate's Sword is available in pretty early game though it's a relatively weak weapon with only a Speed Buff. The Pirate Double bed is available from The Furniture Catalog as you will be passing up Penny on this save. You cannot get Penny's other 2 Pirate options in any other way, though. In fact Penny is a good option for a Pirate theme. But but but Emily's Parrot.
Choices.
Leather Boots to start and are probably the best conceptually, but for sprite looks
Cinderclown Shoes or Dragonscale Boots may be preferable in late game.
Also in late game you could choose to keep
Birdie's Pirate Locket and display it on a Table in the Farmhouse. Your call for how strongly you want this theme.
I'd probably want to design the Farm like a giant Pirate Ship, so choosing the regular Farm layout for it's freedom of space is probably best. That might be the most fun part of the whole exercise, laying out and executing the Ship design in SDV Planner. I'd try somehow to have a gangplank leading to the center bottom lake but it's pretty big and may cut into the design.
Hmmm, for the playthrough there clearly would be a lot of Fishing, maybe using that as your primary source of g, though that will obviously be restrictive in midgame when Farming and Processing are high-g options. Mead (from Honey), Beer (from Wheat), and Winemaking (straight Grapes, maybe Crystal Fruit for the desperate Winter Pirate?) are consistent with Pirates and should mitigate that somewhat. You can't even process anything like Rum or similar from Sugar, so probably Kegging (sugar) Beets to make Beet
Wine lol,
Juice would be the closest in-game analog?