This might sound like an goofy question but it's something I can't stop thinking about whenever I see rennacense art.... Why is Odysseus always depicted wearing what looks like a beanie? Was it something cultural or just.... He was drawn/sculpted like that
Hahahaha not at all! It is actually a pilus hat or pilaeus hat (Greek πῖλος felt).
Typically expected to be made out of wool but also leather and other simple materials, was a hat associated with worksmen, sailors and travelers. It is rather simple to its making and conception, keeps the hair intact under it and can keep the head warm if working outside or sailing. Later it became also a helmet when made out of material like bronze. Generally associated with Odysseus because of his attributes as a sailor and a traveler but also, daresay, for his association with certain hand labors as well such as craftsmanship or carpentering. Also associated with his aliases as someone fallen from grace that now lives among the classes of worksmen or beggar-travellers.
Another hat associated with Odysseus is the Petasos hat (πέτασος)
This broad-rimmed hat was also made out of wool, felt, animal skin or most typically out of straw and was shown to be kept in place with a piece of string that would allow it to hang from the person's neck. Also associated with travelers and moving merchants hence also being associated with Hermes.
Both hats seem to indicate the identity of Odysseus as traveler and sailor.