There are a couple references in the gospels indicating what Jesus wore but not many. His undergarment was 'seamless' according to John 19:23. He also may have had the 'fringes' or 'tassels' of the garment that Jews wore as we see a woman touching a 'fringe' of his outer garment in Mathew 9:20. Many think this indicates that he followed this Mosaic law with regard to dress:
The Lord said to Moses, “Speak to the Israelites and say to them: ‘Throughout the generations to come you are to make tassels on the corners of your garments, with a blue cord on each tassel. (Numbers 15:37-38, NIV)
However, if Jesus wore these tassels, they would not have been like those 'extra long ones' wore by the Pharisees, for Jesus said:
“Everything they do is done for people to see: They make their phylacteries wide and the tassels on their garments long. (Matthew 23:5, NIV)
So here are some references to lead to various sub questions. Did Jesus wear sandals? Would he have worn a Jewish turban outside? Would anyone one notice that he was a teacher buy his dress, or was he just a regular looking guy? Or is this all mere speculation and unanswerable?
The question is, if we were casting a Jesus movie, what clothes did Jesus most likely wear as a combined set? The question is not pointed at 'one' specific article but the combination of articles and the impression, if any, that they would make on a stranger, whether Jew or Gentile.
Note: A related question about the phylacteries or tefillin can be found here.