This question is one that I often get. It seems, especially verse 16, creates a lot of confusion about keeping the feasts and keeping the Torah. Lets look at this section of scripture, and see if we can interpret it to not contradict scripture.
Let no one therefore judge you in eating or in drinking, or in respect of a festival or a new moon or Sabbaths – which are a shadow of what is to come – but the Body of the Messiah. Let no one deprive you of the prize, one who takes delight in false humility and worship of messengers, taking his stand on what he has not seen, puffed up by his fleshly mind, and not holding fast to the Head, from whom all the Body – nourished and knit together by joints and ligaments – grows with the growth of Elohim. If, then, you died with Messiah from the elementary matters of the world, why, as though living in the world, do you subject yourselves to regulations: “Do not touch, do not taste, do not handle” – which are all to perish with use – according to the commands and teachings of men? These indeed have an appearance of wisdom in self-imposed worship, humiliation and harsh treatment of the body – of no value at all, only for satisfaction of the flesh.
As a start, we have to realise that Paul here, is talking to former pagans. They were of the “flesh” (Romans 8:1-8 , that you can read of here) tells us what Paul defines as the flesh, and so does the book of Galatians – Gal 5:19-21), and did the works of the flesh.
Secondly, we have to interpret these verses in a manner that will be consistent with the rest of scripture. If Paul wrote here, that we are not to be judged for eating and drinking whatever we want, by those who keep the law, then he would be contradicting the rest of scripture. Yeshua Himself said that no yod of tittle of the law will change, while heaven and earth exists. And even Paul Himself says that we are to keep the law, and the feasts (Rom 3:31 & 1 Cor 5:8, Rom, 2:13, Rom 7:12), so if he tells us here that we are to not care about what we eat or drink, or which day we keep set apart as the Sabbath, then he would not only be contradicting the rest of scripture, but also himself.
If we look at Acts 15, we see that James gives a verdict, speaking of 4 laws that the gentiles (the Colossians were former gentiles) should keep for a start, and then they are to attend the synagogues, and learn the rest of the law at a pace they can manage, which is preached every sabbath in every city (Acts 15:21). So, these gentiles would, consistent with the words of the book of Acts in general, cleanse themselves of the 4 basic things, and then start to learn the law, so that they can identify sin, and live lives holy and set apart to Father YHWH.
Now, if you take the above into account, Col 2:16-23 takes on a whole new meaning. These Colossians, formerly pagan gentiles, have started to learn about the law, and started to apply these principals to their lives. They started to keep the seventh day of the week as the Sabbath, and not the first day of the week, the venerable day of the sun, made holy by the pagan sun-god worship practicers, including much of the other religions of the time. They started to eat according to the laws of Lev 11, and they started to keep the feasts.
Their former friends, pagan gentiles, then started to judge them, and Paul said that they should not be judged by those who walks according to the flesh. Further more, according to Paul’s words, only the body of Messiah should judge themselves (so only a believer may judge another believer. A believer may not judge the world, since only YHWH judges the world – funny how believers today do exactly the opposite, isn’t it? – excellent point, thanks brother Zachary Jefferson!).
He gives us a big clue that he was truly speaking of those who walks according to the flesh. Verse 18, worshippers of angels, puffed up by his fleshly mind. Again, Paul defines the fleshly mind over here:
7 Because the mind of the flesh is enmity towards Elohim, for it does not subject itself to the Torah of Elohim, neither indeed is it able,
8 and those who are in the flesh are unable to please Elohim.
So, we see that Paul defines the mind of the flesh, as a mind that cannot subject itself to the law of YHWH, and that this mind of flesh is unable to please YHWH. This should give us an incredible insight into the rest of Paul’s letters. We also see that Paul defines the Torah, the law of YHWH, as spiritual, in Romans 7:14
Paul also tells us in verse 20 that we died from the elementary matters of the world. A study of this term will bring you to the conclusion that the elementary matters of the world, is the works of flesh (as defined above), and he then goes further to define it as the commands and teachings of men (contradicting the commands and teachings of YHWH).
The regulations in verse 20 refers to the commands and teachings of men, not that of YHWH.
If we keep in mind that Paul cannot be creating a new set of rules, or that Yeshua could not have come to create a new set of laws/rules to live by, then things become a bit easier to understand in their proper context. All of the NT, including Paul’s letters, are explanations of the OT. It cannot contradict. We see this clearly in Acts 17:10-12, where Paul preached to those in Berea. Those in Berea searched the OT scriptures (that’s the only scriptures they had) every day, to test what Paul said, whether it was true or not. They would not have been able to find agreement in the OT to Paul’s words, if Paul was contradicting the OT with new statements and sayings.
By the above interpretation, we can see that Paul did not preach against the law, and that he, as per his words in Acts 28:5
8 while Sha’ul said in his own defence, “Neither against the Torah of the Yehuḏim, nor against the Set-apart Place, nor against Caesar did I commit any sin.”
So, either Paul lied, or he preached, and kept, the Torah.
I hope this explanation has blessed you, and that it put your mind at ease about this section of scripture.
Shalom, and may YHWH bless you in your reading and studying of scripture.