In Matt. 22:2, Jesus begins a parable about the marriage of a king’s son. In vs. 11, the subject of a wedding garment is brought into the story. Just what does this garment signify, and what is Jesus saying by high-lighting this event? There is no decisive historical evidence about what this "wedding garment" was. Some have suggested that it was a clean, or appropriate item of clothing that would be given by the host to travellers who arrived and did not have clean attire for the celebrations. Others have suggested that it was a special garment used for festive occasions, or even especially suited for attending a wedding. But I don't think that just what it was is the important point of this part of the parable.
This parable follows the statement in Matt. 21:44 that "the chief priests and Pharisees... perceived that He spoke concerning them." Then, in 22:1, Jesus "spoke unto them again by parables..." So it follows that this illustration about the marriage of the king's son also applies to the leadership of the Jews. So the invitation went out (vs. 5), "But they paid no attention and went off -- one to his field, another to his business..." This is saying that the Jews ignored Christ's invitation and announcement of the commencement of the kingdom (figured here by a wedding ceremony). Then He says that "the rest seized His servants (here a figure of Christ and His disciples), mistreated them and killed them (first Christ, later the disciples). Note what He later said in ch. 23:34-36, that upon them may come the judgment for all the righteous blood shed upon the land (most translations read: earth; the word has both meanings, but the context is the land of Israel).
Then, back in 22:7, we see that the King sends armies and destroyed those murders and burned their city (i.e., Jerusalem, AD 70). Now we see the gospel (figured by the invitation to the wedding) going to the streets (vs. 9) to invite "anyone you find." The "chosen people" (vs. 8, those who were first invited) were not worthy of the call, so the kingdom (or: reign) was extended beyond the Jews to the Gentiles -- whoever they could find, (vs. 10), "both wicked and good" (no need of self-righteousness here, it is now a gospel that includes all, not just the chosen ones or holy folks).
So, in this context, we find one without wedding apparel -- keep in mind that everyone else there were street people, yet they all apparently had the correct apparel. I suggest that this would apply to some of the Jews who for a time followed Jesus and wanted to be in on God's present "move of God." But they were there in their own, probably everyday, clothes. They were not wearing a "garment of the kingdom," or, perhaps, a garment of "His righteousness." This one was not killed, as the others were (AD 70), but he was excluded from participating in what was happening at that moment in the kingdom. He would weep and gnash his teeth -- a figure of sadness and regret -- for having missed out on the celebration, and on participation in what God was at that time doing. It's the same story of the foolish virgins missing out on the wedding festivities. Israel was for a season going to be broken out of the olive tree (the source of God's anointing) -- but they could later be grafted back in again. The plan of God's ages has a happy ending. He gives this work to a "little flock," but they are intended to spread His life and love unto the ethnic multitudes, until eventually all return "into Him" (Rom. 11:36).
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