Dean probably found that jacket in a thrift store, and he has a lot of hangups about spending money on clothes when his old clothes fit perfectly well (residual habit from childhood - John hated spending money when he didn't need to) but he looked at the jacket again and tried it on, and it fit so well and it had so many pockets, so he shelled out the $15 to take it home, and it brought him a little joy during a time when everything else in his life seemed bleak (this was s7, remember?) from saltfree
nooooooo kelsey ;A;
what if he went to the back store multiple times before he convinced himself to buy it, cause they were in town a couple days and more than once Dean found himself walking past it, and every time, the pull towards the door tugged a little tighter.
he tried on the jacket 5 times across 2 days before he finally bought it, after the sales clerk on the second day, a cute, young guy who couldn’t be more than 25, by Dean’s guess, finally came over and asked if he needed some help. when Dean declined, the clerk gave him an appreciative once-over and told him he looked good in it. Dean gave him a gruff thanks to cover his blush, but promptly bought the jacket.
before Sam met him back at the motel, he spent 20 minutes just checking himself out in the bathroom mirror, smiling :’)