Dean doesn’t have many ‘pajamas’ necessarily. Always being on the move, clothes for different occasions weren’t really a priority. That space was for weapons and hunting supplies.

He sleeps in what he wears on the daily. Jeans and t-shirts.

That’s why it shocks you when he walks out to the kitchen in a new shirt.

“What is that?”

“What is what?”

Dean looks over his shoulder confused as if he has forgotten the very shirt he purchased, brought home, and put on.

Then you gesture down and he looks, then a stupid grin graces his features.

“Oh yeah.” He says and meets your gaze, “What can I say? It spoke to me.” He shrugs.

Dean has just woken up, still a bit of a grump with a need for caffeine. Hair spiked up with a bedhead and a lazy smirk on his face.

He’s in a grey plain old t-shirt with the words ‘Hard to kill Easy to fuck’ in red bold lettering to match the bold statement on it.