In this week’s Haftarah, Hashem gives Mussar to the Jewish people, as the Pasuk states (Amos 2:6): “For three transgressions of Israel and for four, I will not return them; for selling an innocent man for money, and a poor man for shoes.” Rashi’s commentary doesn’t seem to indicate any connection to the Parsha, but it’s clear from the Midrash that this is referring to selling Yosef. The Pirkei D’Rebi Elazar (Chapter 38) states that they sold him in exchange. After all, the Rishonim are bothered by the fact that Yosef was sold for 20 Kesef, as that is a very cheap price for such a strong young man like Yosef. The son of the Rambam, Reb Avraham, writes that the brothers sold him for such a paltry sum because they were not doing it for money; rather, they just wanted to get Yosef away from Yaakov. However, the Midrash says that each brother gave two Kesef and bought shoes. This is why the Pasuk (Bereishis 37:28) states that they sold Yosef to the Ishmaelites for 20 pieces of silver.
The question is, why did they specifically buy the shoes? The holy Beis Yaakov explains (based on the Gemara [Ta’anis 23b]) that one of the great Tanaim put on shoes whenever he traversed through water because he didn’t know what was in the water. The hidden aspect of shoes is to protect oneself from questionable impediments. When one wears shoes, they are saying that they are secure in uncharted territory. When it comes to Yibum, the Gemara (Yevamos 39b) says Reuven can’t marry his brother, Shimon’s wife, but if he dies, there is a Mitzvah for Reuven. However, Abba Shaul says that Reuven cannot marry her for her beauty or relations, it is forbidden like an Ervah is forbidden to a man. If there is a child that comes out of this union, he is a Mamzer (illegitimate); this is because this Yibum was done without the proper Kavanah.
The Beis Yaakov says that a person who does not want to get into such a situation does chalitzah, which is consummated by the removal of one’s shoe. What is the message here? The idea is that one must be sure to do Yibum, and that it is selfless, and the removal of the shoe represents playing into this uncertainty. We also learn in the Parsha about Yehuda and his incident with Tamar; Yehuda was confident that he did it Leshem Shamayim, whereas Yosef could not say with any certainty that Eishes Potiphar was permitted to him (although he did marry her daughter, Osnas). He explains that the selling of their brother Yosef was a very questionable act to the untrained eye, so the brothers bought shoes to indicate surety in a place of doubt.
The Midrash teaches that they made a cherem not to tell Yaakov and Hashem joined this cheirem, as well. These people were kedoshim and tahorim, holy and pure, but still the Navi rebuked them that somehow this super-confidence was not called for, and Hashem had a problem with that certainty on their level. When it comes to certain things in our lives, we sometimes put on our shoes and go; however, it’s better to always ask a Rebbi, mentor, or friend for feedback before entering uncharted waters.