Lotr headcanon, having lots of patches on your clothes is fashionable in the Shire. The more patches, the cooler you are. Especially if it's a lot of different fabrics. It's common to trade patches with friends and family, and it's usually treated with high sentimental value. It's like carrying a piece of someone with you.
While the hobbits are on the quest, their clothes get holes and such. This leads Sam and Frodo to nab small things from the other members of the fellowship, like handkerchiefs or anything too worn for use, to use as patches. Merry and Pippin aren't so courteous, and cut pieces from the fellowship's clothes while they sleep.
Of course, the hobbits exchange patches amongst themselves while traveling, and they never go anywhere without a needle and some thread. Sam is the best at sewing. Pippin is not allowed around needles.
Boromir notices this, thinks it's adorable, and leaves things out purposely for the hobbits to use. Eventually, he asks about it, and they convince him to do the patches, too.
Aragorn also notices and thinks it's adorable, but doesn't bring it up to them. He's secretly flattered to find pieces of his rag on Frodo's pants. He asks Boromir about it instead.
Legolas doesn't notice. His clothes are elven-made, and the scissors refuse to cut it.
Gimli notices the random holes in his clothes, and the things going missing, but doesn't realize it's the hobbits. He brings it up to Legolas, who immediately convinces Gimli that he's crazy and it's all in his head.
Gandalf notices, obviously, and he doesn't mind until Pippin tries to cut his cloak while hes asleep. He proceeds to wake up and yell at him until dawn.
After Boromir dies, Aragorn takes his cloak, and sews pieces onto his clothes. These are the only patches he has.
Bilbo has a set of clothes with patches from the dwarves, from his own adventure. He told them about the tradition, and they all gave him pieces of fabric to use. He can still recount which patch belonged to who.
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