His Clothes That You Wear--
Dean: you wear his T-shirts, sometimes you sleep in them. And sometimes you just wear them under a sweater or flannel.
Sam: his flannels. Always. All the time.
Cas: when Cas isn't all dressed up in his trench coat, he sometimes wears a blue hoodie. You wear that hoodie quite often, but it's still his.
Adam: you wear Adam's basketball shorts, they are floppy and comfortable.
Gabriel: you wear his sweatpants. Especially when you are tired or it's a rainy day.
Lucifer: you take his hat. When he goes out he wears a beanie most of the time, but he's got a bunch of them. So you take one and wear it sometimes.
Balthazar: you wear his V-neck T-shirts, only at home though.
Gadreel: you steal his jackets, but always give them back. He's a little confused as to why you do that, you have your own. But he lets you do it, because it's not hurting anything and it seem to make you happy.