Then He spoke a parable to them: “No one puts a piece from a new garment on an old one; otherwise the new makes a tear, and also the piece that was taken out of the new does not match the old. 37 And no one puts new wine into old wineskins; or else the new wine will burst the wineskins and be spilled, and the wineskins will be ruined. 38 But new wine must be put into new wineskins, and both are preserved. 39 And no one, having drunk old wine, immediately desires new; for he says, ‘The old is better.’” — Luke 5:36-39, NKJV

Having just told the parable of fasting at the wedding feast, Jesus goes on to tell the parables of the cloth and the wineskins to further draw the distinction between the new and old covenants, and between His teachings and that of Judaism.

The Pharisees of Christ’s day, while accepting scripture as the inspired word of God, had over time placed equal emphasis on man-made religious traditions and an unconfirmed “oral law” claimed to have originated from Moses. These practices in effect added to the word of God, a heresy by definition and a major source of conflict between Christ and the religious establishment.

He begins with the cloth illustration. Matthew and Mark use the word agnaphou (unshrunk) in describing the piece of cloth taken from the new garment, which makes plain why the “new makes a tear.” When an unshrunk patch sewn onto an old garment inevitably shrinks, it is going tear the older material it’s affixed to. Just as new and old cloths are incompatible and do not match, Jesus’s message of grace cannot be mixed with pharisaic practices and traditions.

He next gives the example of new wine in old wineskins, which paints a similar picture of unsuitability. New wine had to be stored and repeatedly transferred into new, supple skins while it completed the fermentation process, as unfermented new wine would rupture the old, inflexible skins as it expanded. In the same way, the gospel of grace, faith and repentance does not conform to the legalistic, works-based platform of the Pharisees. God’s truth does not assimilate to man’s flawed religious constructs.

Finally in verse 39 He addresses the reluctance of those fully vested in traditional Judaism to embrace the gospel. Comfortable and content in their familiar rituals, doctrines, and prejudices, the religious establishment was addicted to their particular brand of heresy. This put them at a disadvantage when it came to recognizing and embracing real truth. The same can be said of followers of all false religions.

What was most importantly missed by the Pharisees was the fact that through Jesus, the new, better covenant was realized— one which made unnecessary the ceremonial aspects of the Mosaic law and temple ordinances in which they based their faith. In Christ, believers are no longer under law but under grace.

Still, in considering the parables of the cloth and wineskins it is very important to understand that Christ is not invalidating the Old Testament or contradicting Himself in New Testament passages such as Matthew 5:17-18 or the parable of the householder. When Jesus refers to the "old" cloth and wineskins He is not talking about the Law and the Prophets. We must remember that He came to fulfill the law, with not one jot or tittle to be discarded. Specifically He is drawing the distinction between His teaching and traditional Judaism, but in essence He is declaring the gospel's incompatibility with any other religion. God's holy truth supercedes all.