One must have a good understanding of not only the OT, but people have no clue about the Customs of the Hebrew people at the time these Scripture's were written. If you search out the difference between the [LAW] Torah, and the Oral Torah, then one might have a better understanding of What Our Savior was dealing with concerning the Religious Leader's during His Ministry!
Take for instance, you have a Bible, Ok, within that book there are 613 binding Commandment's in the OT, mainly in the first 5 book's.
Some were for children, some were for women, and some were for men, and then some were for the Levite's among the men, some were for the Priest's from Aaron's family, and then some for the High Priest.
If one take's the time you will find that the Commandment's specifically addressed to you would be fewer than you think!
NOW, here is the Stinker, The Pharisees had not only departed the Law of Moses, But had committed the Major Transgression by adding hundreds of Commandment's, and Also removing Commandment's, they had instituted a Religion of their Own, for at least 300 year's before the Birth of our Savior. A Man Made Religion, and to this day it is now called Judaism! In so much that the Oral Torah is now, and has been written, there are 22 Volumes of rule's and regulation's and Commandment's of which they were Burdening the People, then and up to this day! So if you take this Info into consideration as you read, you might be able to distinguish the difference. Most of the time where the word Jew is used in the new Testament, you might read it as Pharisees, because they had come to believe in the Savior, But were still trying to inject the Oral Torah, which is just a bunch of Hogwash, MAN MADE, MAN MADE Commandments!!!!!!!!!!!!!!
And as far as the verse Colossians 2:16 Paul had preached to the people in Colossian, and they had received the Promise! So let no men that are still worshiping Pagan Deity's Judge you in Meat, or drink, or in respect of a Holy day, or of the new Moon, or the Sabbaths.
This also pertains to Colossians 2, The hundreds of Commandments that the people were being burdened with, Hand writing's, and ordinances.
Our Savior said that the Truth will set you free!!! Free from What, Free from Man Made Religion. This is why our Savior was constantly insulting the Religious Leaders, You Hypocrites!!!! Think!