Sam is going to be really, really boring. Victorian/Edwardian tux, just...a lot longer than people are used to making them. I'm sure the tailors will have a moment because they'll probably have to whip up his trousers very, very quickly.
The main thing that's going to be different from this world is that he'll have a padded shoulder for his red-tailed hawk. I'm going back and forth on whether the hawk is named Jess or Eileen. >.> No, my shipper heart has nothing to do with this.
Or possibly this one. But I like the longer coat and Remy would as well. Especially if he could get the tailor to add some extra pockets to the inside.
SAM, on the other hand, will stand out. He's literally been touched by an angel (two, even: Lucifer and Castiel) and his soul is far, far older than his body. Therefore, he's going to have a LOT of Dust.
No, I'm not considering Gabrielle for Sam's because it's hilarious.