Go off the angle of the sails. The flag should follow apparent wind direction.
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Depends on the point of sail, that is, the direction the ship is sailing relative to the wind.
Broad reach / running downwind - the flags point toward the bow.
Close-hauled / tacking upwind - the flags point at an angle, somewhat toward the stern.
Go by the diagram here: https://en.m.wikipedia.org/wiki/Point_of_sail
The flags will point in the direction of the wind arrow. ⬇️
I think it might be a bit of wishful thinking that a square rigged ship could run close hauled. At least that's my impression of pirate ships.
Also what I wanted to add not all paintings are physically accurate on sails and wind direction.
I once played a game of from how many directions does the wind blow on this painting, and this was in a maritime museum with paintings depicting sea battles. (and a lot had the "problem" of every ship had it's own wind)
so what I wanted to say, is if you aren't trying to depict really accurate the ship anyways. (as to me Pirate ship sound like a really bad generalization of ships types.) Do whatever you like looking at the best. And otherwise, follow u/swope 's advise.
Depends on what point of sail the ship is going in. The flag could be blowing any number of directions. What is your model rigged for?
It's a very cartoony small brig I think. Realistically it's meant to look more like the idea of a ship than anything that could actually work as one.
In that case, personally I'd make the flag blowing toward the stern to show that it was beating up wind. I'd upvote a picture of the completed model if you upload it 😁