To fully comprehend the parable Jesus shared regarding old garments and wineskins, we can draw upon select passages from Paul's letter, accompanied by insights from John Chrysostom.
Apostle Paul confronted Apostle Peter, contending that, as a Jew, he lived like a Gentile by not adhering to the Jewish law, yet he was imposing Jewish customs on Gentile believers, demanding that they follow all stipulations of the so-called Jewish law. Paul emphasized that justification cannot be achieved through the works of the law, but is found in faith in Jesus Christ and adherence to His commandments. If one believes justification comes through the law, Paul argued, then Christ's sacrifice was for naught (see Galatians 2:16-21). John Chrysostom further expounded on this, warning that compliance with the law would nullify the Gospel. He reasoned that if the entirety of the law were required, then justification by faith would be undermined. He questioned the implications of observing the Sabbath without circumcision or making sacrifices if circumcision was embraced. Chrysostom concluded that if it is necessary to fulfill the entire law, following Christ would either lead to a rejection of Him or result in being labeled a lawbreaker, attributing any transgression to Christ since He permitted deviations from the law.
Returning to the parable from Jesus’ perspective, we know the Pharisees frequently criticized His disciples for their disregard of the law, such as harvesting grain on the Sabbath, failing to fast, and eating without ritually washing their hands; Christ defended them each time. In response to the Pharisees and John’s disciples accusing them of not fasting, the Lord again defended His disciples but extended His argument to articulate how His teachings contrasted with the strict observance of Jewish law. Through this parable, which invites various interpretations, we can align with the understanding suggested by Paul and Chrysostom: "You (Pharisees) wish for My disciples to don the old garments of your legalistic practices and traditions, while I urge them to wear the new garments of love and forgiveness. It is essential to shed the old attire before adorning the new. You cannot mend the worn-out garment by using pieces from the new; instead, the old garment will be further damaged. Likewise, just as young wine cannot be contained in old wineskins, I encourage My disciples to embrace the new teachings and allow themselves to be transformed. Though they are still growing in understanding, they recognize the superiority of My teachings, just as one accustomed to fine wine would avoid inferior quality. The statement that 'no one, after tasting old wine, desires new wine' (Luke 5:39) might appear contradictory in light of the message regarding old garments. However, this confusion clears when we acknowledge that old wine is typically regarded as good, while new wine may seem less desirable, which clarifies the purpose of the parable. Indeed, no one who has enjoyed excellent wine will swiftly choose a lesser variety."