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.

Truthfully, between the brothers, Dean is actually the one with any ounce of sewing skills. Mallory always took care of it for her tall boys, and Krissy helped get Sam a few new sets of clothing when he was last at Trails West. 

On the other hand, Dean dealt with being a hunter on his own for years before he met back up with Sam. Clothing rarely comes with the number of pockets he uses, and he has to repair his clothing a lot from being on the job. Bobby was sure to make sure a young Dean knew his way about a needle, both with clothing and skin, while he was growing up, and no matter how much Dean bitched about it.