Our Gemara on Amud Beis relates an interesting story about Rabbi Eliezer Ze’eira:
Rabbi Eliezer Ze’eira was wearing black shoes, unlike the Jewish custom of that time, and standing in the market of Neharde’a. Officials of the house of the Exilarch found him and said to him: What is different about you that causes you to wear these shoes? He said to them: I am wearing them because I am in mourning over the destruction of the Temple and Jerusalem, and so I wear black shoes, as is the custom of mourners. They said to him: Are you a man of such importance to publicly mourn over Jerusalem? They thought that it was simply presumptuousness on his part. Since he was acting against the prevalent Jewish custom, they brought him to the prison and incarcerated him.
Eliezer Ze’eira said to them: I am a great man, a scholar, and it is fitting for me to mourn publicly over the destruction of Jerusalem. They said to him: How do we know that you are a scholar? He said to them: Either you ask of me a matter of halakha and I will answer you, or I will ask you a matter of halakha and you will answer me. They said to him: You ask.
He said to them: With regard to one who cuts a cluster of flowers on the stem of a date palm belonging to another, what is he required to pay? They said to him: He pays the value of the date stem. He said to them: But ultimately they will become ripe dates, which are worth more. They said to him: If so, he pays the value of the future dates. He said to them: But he did not take ripe dates from the other person, so how can the court obligate him to pay for damage that he did not cause?
They said to Eliezer Ze’eira: You tell us the correct appraisal for the date stem. He said to them: The court appraises the damage relative to a similar piece of land sixty times the size. They said to him: Who says an opinion as you do, so that you can prove you are correct? He said to them: Shmuel is alive and his court exists; you can ask him. They sent the question before Shmuel, together with the ruling of Eliezer Ze’eira. Shmuel said to them: He is saying well to you, because the halakha is as he says; the appraisal is relative to an area sixty times greater. Upon hearing this, the officials of the Exilarch realized that he was a great man and they released him.
Rabbi Yonasan Eibschutz (Yaaros Devash I:16) has a wonderful and creative interpretation for this aggadah:
He starts with discussing how shoes came to signify mourning for the Beis Hamikdash. He argues, since in the time of the Beis Hamikdash the Shekhina was present, holy people would suddenly experience Ruach Hakodesh and thus feel compelled to remove their shoes, as we see when Moshe first encountered the Shekhina at the Burning Bush (Shemos 3:5). (I believe the “removing of the shoes” really means divestment of physicalities and externalities. Rav Eibschutz did not spell this out, possibly because he felt it was a mystical concept that should be known by those who are worthy, and if you do not know then you weren’t meant to know it, as with many matters that are mystical.) However, to express mourning in this manner implies that you feel yourself worthy to have received Ruach Hakodesh, hence the reaction that he was breaking social boundaries and protocols.
Yet, there is another reason for wearing shoes to signify mourning for the Beis Hamikdash. The cause of exile is attributed to the sale of Yoseph by his brothers to the Ishmaelites in exchange for shoes, as described in Amos (2:6). The actual sale of Yoseph was rationalized by the Shevatim as a pre-emptive strike against a would-be usurper, similar to how their father viewed Esav, and their grandfather viewed Yishmael. (That’s a lot of family dynamics! But, we will discuss that at a different time.) In the end, Joseph was vindicated and the brothers were proven to have acted in haste with poor judgment. This is hinted at in the discussion between Eliezer Ze’eira and the Exilarch’s henchmen. The “cluster of flowers on the stem of a date palm” represents Yoseph’s unrealized potential. A Tzaddik is compared to a blooming date-palm (Tehilim 92:13), thus the discussion about the value of the damaged date-palm is a discussion about the haste of shevatim to convict Yoseph before he fulfilled his potential. And this aspect of signifying mourning through shoes could be made by anyone, thus Eliezer Ze’eira defended his practice as not presumptuous. (Also, I would say that he also was hinting that he too, was misjudged, like Yoseph.)
In contemplating Rabbi Eliezer Ze’eira's story we find a man who walked “in the shoes” of different eras and experiences. He may have seemed “out of step” with what were the standards of the day, but he definitely had “sole”.