A marriage has been arranged for the king's son, and the initial invitations were sent out so all on the guest list could make plans to attend. In those times, travel over long distances was far slower than today, so plans needed to be made long in advance. However, those invited, though possibly honored by the invitation, declined to attend the wedding.
So, a second, more urgent invitation was sent out to the same people, as time was getting short, but the invitees paid little heed to it, caught up in their own activities and ventures. They stated by their actions that they cared little for the king and his son. In fact, they were sufficient unto themselves with their farms and shops; they felt they had need of nothing (Revelation 3:17).
Proving their contempt, they treated the king's servants, who had personally borne the invitations to them, with great disrespect and even killed some. The king was rightly furious, and he mustered his forces to avenge his maltreated servants to erase the disrespect shown to him. His kindness and generosity had been spurned, and he responded with wrath.
A third invitation had to be sent. For this one the guest list changed from the specially invited to the everyday person, some of which were good while others were bad. In this way the wedding was finally furnished with guests.
The custom in those days was for the one hosting the wedding feast—in this case, the king—to provide garments for the wedding guests. These wedding garments were simple, nondescript robes that all attendees wore. In this way, rank or station was covered, so everyone at the feast could mingle as equals. Revelation 19:8 defines this symbol: The wedding garment identifies the righteous, those who lived according to God's ways.
When the king entered the wedding hall, he noticed that one guest clearly stood out from all the others because he was not wearing a wedding garment. Having the man brought forward, the king asked: “Friend, how did you come in here without a wedding garment?” (Matthew 22:12). The sense of his question is one of incredulity. It might be better phrased, “Why are you not wearing a wedding garment, even though one was provided for you?”
The man was plainly not dressed correctly for this occasion. His lack of a wedding garment was another example of extreme disrespect for both the king and his son. The wording, “And he was speechless,” indicates that he was without excuse. It was not just that he lacked a wedding garment, but that he did not wear one on purpose. He had defiantly refused to put one on.
This is why the king reacts so swiftly and harshly: “Bind him hand and foot, take him away, and cast him into outer darkness; there will be weeping and gnashing of teeth” (Matthew 22:13). His judgment is not against the man's lack of a wedding garment per se, but that he did not intend to wear one. He was, in fact, determined not to wear one.
The man desired the honor of attending the wedding feast, but he did not want to follow the custom of the king. He wanted to do things his own way. His lack of proper dress revealed his inner rebellion against the king and his instructions. He was executed as a rebel.
It is here that Jesus inserts His somewhat cryptic phrase, “For many are called, but few are chosen” (Matthew 22:14). God's calling clearly corresponds with the king's invitation, and indeed, the invitation went out to both the original guest list (Israel/Judah, whose people were killed in war and whose city, Jerusalem, was burned; Matthew 22:7) and then to mankind generally. We can conclude that, while God's calling is widespread—going to “as many as [His servants] find” (Matthew 22:9)—those who respond to His invitation and whom He subsequently chooses to wear a wedding garment are a far smaller group.