@SheSawSeaShore, I've been doing the same and am making sure I wear every piece of knitwear I own this winter.
The idea of a holiday packing list sounds good. I often pack a load of things that in theory I could wear together, but by the end the only things I have left don't match and my last few days I'm trying to put together whatever I have left that's clean.
I'd like to pack whole outfits with options, like a pair of trousers with 3 t-shirts specifically to wear with them and actually try and stick to that. The Whering App might help.
Last summer I tried packing things together in outfits but everything got mixed up and I didn't stick to them.
I think such planning would involve a big trying on session of various outfits in advance and recording them on the Whering App in a packing list. And then actually looking at it when getting dressed.
Only problem I find is, it needs a bit of flexibility as sometimes things unexpectedly get dirty, especially trousers, so t-shirts would have to be wearable with more than one pair in case their intended partner trousers end up in the laundry bag.