I don't know if you have noticed, but they have some serious clothing issues in season 12. Seasons 1-11 we just had Sam and Dean. But now that there's Mary, they can't all wear plaid. Because there would be too much flannel with three Winchesters. I'm being serious. I've rewatched season 12, and there's no episode where all three Winchesters wear plaid. One of them always has to sacrifice the hunter look.
Yeah, they don’t all wear it all the time anyway - Dean’s always had a bunch of stock shirts which are so boring he can wear them all the times he’s going to get killed or whatever gets him covered in blood to the point that he can’t use it any more :P Sam has slightly more variety, I think, because he doesn’t wear as many block colours in general, wears his shirts buttoned up so Dean can get away with wearing a block colour shirt and t-shirt, and Sam’s on the wrong side of the self-imposed class divide so doesn’t wear henleys either, all adding up to him needing at least subtle stripes on his shirts a lot of the time… Sam wearing boring grey in 11x22 should have been a warning something pretty horrific was going to happen to him because that’s Dean’s choice of colour for “I’m about to have a bad day and I don’t know it yet” which he at least also mixes into his regular wardrobe to add the element of surprise :P
Buuut yeah I bet there was at least 1 time they had a moment where they did all wear plaid and looked at each other and had to work out who had to go change immediately.
Anyway since we have a whole season now, let’s look at Mary because I like looking at Mary :D