I'd totally wear the shirt with his sweat and blood on it, and maybe some decorative ichor on the edges to highlight the righteousness of the whole thing. If it got torn in the battle, so much the better.

Note, I have never put on a guy's clothing post-nookie. It seemed weird. My clothes were always right there.

I think Lisa would wear the green long-sleeved henley, because it would hang to a short nightie length on her, and it would be super soft and smell like him. Plus, he would like the flash of cleavage if she leaves it unbuttoned.

Cas would wear Dean's Dark Side of the Moon shirt. Dean wouldn't let Sam wear his shirts, because he rips them sometimes when he twists the wrong way.

And we know Dean wears Sam's clothes in hard times.

But not the funky-print Western-style ones.

I bet half of Dean's flannel plaids *are* Sam's, but Dean has borrowed them so often, Sam considers them Dean's now. And buys shirts he knows Dean will turn up his nose at.

OMG, Lazarus Rising, where Dean comes back from the dead and has no clothes and wears Sam's??? How wonderful was that?

I'm sure Dean regards most of the prints on Sam's shirts the way he regards his music, and fanon has him regarding his hair. But he'd be horrified if Sam started to emulate him. He might be cool, but he's worthy.

Sam probably grew up wearing all of Dean's outgrown stuff. The clothes sharing must go way back.

I would love to read a gen story focusing on the summer (or whenever) when Sam had the last growth spurt before he left for Stanford, and Dean realized Sam was actually taller than he was.

I went from shorter than most of my relatives to skinnier than most of them, so I was always prime hand-me-down territory. No skin off my nose. I'd bet it would bother Dean, though.

It's mad convenient being my sister's size now though, let me tell you.

I think Dean would subconsciously associate being big brother/protector with needing to be physically bigger. At least at first. I'd hope he's used to it now.

For a while, I was convinced that Dean could still take Sam despite the size difference, because he was wily and a badass.

Now I'm going to have to recuse myself from the debate.

I have a plain T-shirt kink while guys are working on cars. If I'd had Lisa like access, the grey shirt from when Dean smashed up the Impala in Bobby's yard, would still be in my possession. I would sleep in it every night and if it had started to fall apart, I would make it into a pillow cover.

Post intimacy though, I don't think I've ever worn the guys' clothes either. That's not something that ever occurs to me as being cute or endearing as much as "hey look, this is me being a weird girlfriend". In a long term relationship, I might adopt a longer shirt ala Amy's suggestion for Lisa, but it never happened before.

I have to think that Dean had at least a momentary knock to his ego when little brother became bigger than him. Our culture equates taller and bigger with better and more manly, however wrong headed that is. But it's there and would cross Dean's mind.

For a while, I was convinced that Dean could still take Sam despite the size different, because he was wily and a badass.

This was true through the beginning of the series. When was the first time that we saw Sam really "win" in a brawl with Dean? Was it as late as when Dean was lying on the floor telling him if he walked out the door, not to come back, echoing Sir's words. Come to think of it, I think we have approached the time when Sam would be able to over power Sir. Obvs, if Sir were still alive.