Toldos
Rivka then took the chosen garments of her older son that were with her in the house and dressed Yaakov her younger son. Bereishis (27:15)
The Reisha Rav, Rav Aron Levine, writes that when he was a young man he remembers hearing from his grandfather, HaGoan Rav Yitzchak Yehudah Shmelkis, a homiletic interpretation of this posuk.
The word begadim in our posuk, translated as clothing, can serve as a symbol for the character traits of a human being. For example, a posuk in Iyov reads: "I pursued righteousness until I was garbed in it" (Iyov 29:14). We see here that the trait of righteousness is compared to a garment that is now being worn. Similarly, in Koheles we read "At all times your begadim should be white" (Koheles 9:8). This is interpreted to mean that, at all times your character should sparkle like a clean white garment. Using this idea let us reinterpret the posuk.
We know that the character of Yaakov was perfect. He represented the epitome of honesty, sincerity and purity. He did not embody one iota of falsehood. The character of Eisav, on the other hand, was the diametric opposite. He was a murderer, thief and deceiver. Rivka perceived that the only way that Yaakov would receive the berachos would be through deception. But Yaakov, on his own, was not capable of being deceptive. Deception was Eisav's specialty. Rivka was thus forced to dress Yaakov with Esav's trait of deception in order to succeed in directing the berachos to their deserving recipient. This is then the meaning of the posuk; Rivka dressed Yaakov in Eisav's character.
After hearing this, the Reisha Rav questioned his grandfather. If this is indeed the correct interpretation why the does the posuk say that Rivka dressed Yaakov in Eisav chosen clothing? If the word begadim here truly refers to his character then in no way could the Torah call Eisav's character "chosen." The Hebrew word here for "chosen" is chamudos, which has the connotation of honorable and worthy.
Based on the foundation his grandfather had laid, the Reisha Rav suggested an alternative interpretation. We do find that Esav had one redeeming quality, i.e., the mitzva of kibud av. Kibud av is a mitzva that develops good character. The gemara records that Raban Shimon ben Gamliel said that all his life he served his father, but the quality of his service didn't reach even one hundredth of the quality of service with which Eisav served his father. Rivka realized that in this character trait, Eisav was in danger of surpassing Yaakov. Rivka thus took this chosen trait of kibud av and dressed Yaakov, i.e., she influenced Yaakov to follow the example of Eisav and serve his father delicacies in a similar fashion and thus merit to attain his deserved berachos. This then is the meaning of the posuk; Rivka dressed Yaakov in the chosen trait of Eisav, the character trait of kibud av.
With great satisfaction, Rav Yitzchak Shmelkis agreed with his grandson.
