Ah, I missed that it was a prompt.
Nevertheless, it’s not a prompt I’d do with the brothers. Like I said, Sam’s not skilled with sewing in my ‘verse. If Dean saw Mallory or Krissy at work with a needle, he would be in awe, and the same goes for Oscar, who has his own set of sewing supplies. Sam, however, is more likely to make a mess of things while Dean, despite his thread being closer to yarn for Sam, might have a chance of fixing it. It’s just like fixing up doll clothing, which isn’t impossible, especially for a man used to working with intricate equipment and crafting his own weapons.
If Dean saw Sam working in his journal, on the other hand, he’d be awed by the tiny writing that must be microscopic compared to him. He won’t be able to believe how precise Sam’s writing is.