He would have worn the same kind of clothes as any other working class man of the time.
This would be a tunic (knee length) like a Roman tunic. This was usually made from two squares of cloth sewn together, however according to John 19:23, Jesus’ tunic was woven in one piece, without a seam. It would probably have two stripes, running from shoulder to hem. Many tunics like this from the time have been found in caves.
Over this he would have worn a mantle – a large rectangle of cloth which he would wrap round himself, and also use as a blanket at night.
He would have worn sandals. These would have had a leather thong which went between the toes, and a slider to loosen them. Again, sandals from the time have been found.
Round felt caps were certainly worn by some people at the time, though it is unknown if Jesus wore one. (The Arab keffiyeh, which is common today in the region, is a modern type of headdress).