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I've got a coat I wore every winter for like eight years but didn't use this fall because a rain of macroplastics would follow me wherever I go. I can strip the pleather, flaking-paint material off to replace it with something but the fabric underneath is sort of thin and stretchy so I'd need to find something that'll help seal it against wind and rain again. I know they sell pleather paint but reviews said it's short lived or meant for patching lesser damage. It's probably a long shot but is there another option for doing the whole outside of the coat?
Otherwise it's still in great shape.
That's a really cool idea! Tbh when I asked the question I'd been thinking of the old 'oilskins' used by sailors in fantasy books (and history) which I think were sailcloth or canvas coated in tar, so this would actually be pretty close to what I had in mind.
One of my favourite YouTube DIYer NightHawkInLight has a detailed video on it. I'm not sure if it will work for your exact case, but I think I would have gone the same way if I was in your shoes. https://www.youtube.com/watch?v=HedRbIsM75M
I think it was more of a wax type of thing, but those become quite inflexible and might not be nice to wear as a jacket.
Oilskin jackets used beeswax cut with a drying oil like boiled linseed to keep it thin and flexible. The same drying oils get used in oil paint because they polymerize into a nice paint-like finish.