A couple of questions ,Cambria
1) Why are you doing your summer/winter swap now?
Unless you live in the far north of Scotland you have another five weeks or so before you need to go into winter clothes
2) Why do you live in leggings?
Throw them out.
Check out the good clothes you have but never wear and start wearing them every day.
This time last week I was in Keswick.
It was a beautiful day and there were coach trips of ladies of a certain age in the town.
Virtually all of them were dressed in the same way .
Man made brown,beige ,black or navy sensible trousers.,tops covered with cardigans.
I didn't see anyone else of my age wearing a cotton dress .
How depressing it was.
Buy good quality clothes made from natural fibres and they will last for years.
You say you still have the wedding outfit you bought for your son's wedding ten years ago.
Is it an obvious wedding outfit ?
If you go to another wedding will you feel like wearing it?
If not,give it to the Charity Shop.
Stick to a colour palette that suits you and throw out anything that doesn't.
Only wear clothes that make you feel good even when you are not going anywhere special.
As had been said ,it is very cathartic to have a good sort out.
Good luck .