Were some of the biggest moments in Jesus' life when he was naked?

Not quite. His mom wrapped him in swaddling clothes when he was born, so he was not naked. When he was crucified he was stripped and his seamless garment was taken away. Even then, the Romans put a cloak and crown on him, so he was not totally naked. The clothing in the tomb was for a corpse, so it was left behind. When he came back, Mary Magdalena mistook him for a gardener, probably by what he was wearing. Sounds like fun to be -- after all some witches do it and call it skyclad -- but it's not scriptural.