I think this is really interesting--K/P and K/T raise fun questions. The jacket, sure, it's over.
The trench, you look great in, as you can so do in so many things, but it's not really the modern easier fit and look, I guess. So I'd have to be practical--is it a placeholder that you need to have to get around, or is a style-blocker and you'll wear it just because you have it. Or sometimes it's not good to get rid of something if you really don't want to feel pressured into getting its replacement. I think that's the hardest thing. I know the swap is the immediate thing, but sometimes I let retail research help me compare things I have and see if I really ought to move on or if the new items aren't so much different or better after all--as in, I'll wear said items or outfits while shopping. One problem is that sometimes an updated look (or at least what is readily available in stores) doesn't fit my body type or something so I'll have to decide how to use the item that fits well, but plan to mitigate or juxtapose it with other items in the outfit to achieve the update or style shift until there is something really wow to replace it.
Or, you could just take Angie's advice directly!