I wonder how Jesus dressed and did he look like the rabbis of the day. I believe he probably dressed like any other Jewish man because the Samaritan woman knew immediately that he was Jewish but didn’t pin him as a rabbi or holy man until after he prophesied about her. And when he was arrested in the garden, the soldiers couldn’t tell him apart from his disciples. He wore sandals, an inner garment, and an outer garment. And I am pretty sure he would not have worn the phylacteries as that seems against his spirit of piety and sincerity rather than showy sensationalism.
Did he have short or long hair? Pretty sure it would have been short as other scriptures speak against long locks for men. Probably a beard – at least when he came out of the desert after his 40 day ordeal. I just can’t see him carrying a razor around with him, shaving in the Jordan River.
Does it matter what he looked like? I think it does to the extent that he probably didn’t look like the cinematic version of a long haired effeminate movie star. He led a tough life, worked hard as a carpenter, fasted a lot, walked a lot, spent a lot of time in the sun as he worked and traveled from town to town.
He was/is a real man and worthy of hero status and worship.