וְזֹאת֩ לְפָנִ֨ים בְּיִשְׂרָאֵ֜ל עַל־הַגְּאוּלָּ֤ה וְעַל־הַתְּמוּרָה֙ לְקַיֵּ֣ם כָּל־דָּבָ֔ר שָׁלַ֥ף אִ֛ישׁ נַעֲל֖וֹ וְנָתַ֣ן לְרֵעֵ֑הוּ וְזֹ֥את הַתְּעוּדָ֖ה בְּיִשְׂרָאֵֽל׃
און אַזױ איז געװען פֿאַרצײַטן אין ישׂראל: בײַ אַן אױסלײז אָדער בײַ אַן אױסבײַט, צו באַפֿעסטיקן עפּעס אַ זאַך, האָט אײנער אַראָפּגעצױגן זײַן שוך און געגעבן דעם אַנדערן. און דאָס איז געװען צום עדות אין ישׂראל.
Da'at Zekenim
!של, “remove!” the reason why the Torah had to write: מעל רגליך, “from your feet,” when we all know that he was not asked to remove his sandals from his hands, is that there are two kinds of sandals. There is a kind worn on one’s hands. [In fact, in German, the word for gloves is: handschuhe, “shoes worn on one’s hands.” Ed.] This was the נעל that Boaz gave to the redeemer who was first in line to perform a levirate marriage ceremony with Ruth, the daughter-in-law of Naomi. (Ruth, 4,7) As far as the question why Moses had to remove both his sandals, whereas Joshua had to remove only a single sandal (Joshua 5,15), the reason is that in this instance the Presence of the Spirit of G–d preceded the arrival of Moses on that site, whereas in the Book of Joshua, Joshua had already been on holy soil (the land of Israel) before the appearance to him of the angel, i.e. the Spirit of G–d.
Rabbeinu Bahya
A rational approach to our verse: the term של נעליך is not to be confused with the term חלוץ נעליך. Whereas the latter means: ”take off your shoes,” similar to the expression שלוף נעליך, in Ruth 4,7 “taking off a sandal,” or to Deut. 25,9, “she will strip off his shoe,” the word של is related to שלילה, something negative and means that there was no need for Moses to wear shoes in such a place. He was warned to strip off what the shoe represented, i.e. material concerns. The act of removing his shoes was a mental preparation to ready him to become G’d’s vessel, His prophet. The lesson was that just as a man can take off his shoe at will, so he can divest himself of material concerns and concentrate on spiritual concerns. Instead of remaining attached to the עור, the leather of his shoe, he should become attached to the enlightening properties of his illuminating intellect, his אור השכל. When Joshua received a similar command in Joshua 4,15 he was told של נעלך, “remove your shoe (singular).” The difference between Moses and Joshua was that Moses had separated from his wife and was thus able to divorce himself more easily from earthly concerns. Joshua had not. G’d had told Moses in Deut. 5,28: “you- stay here with Me,” something which had enabled him to remain closer to G’d and to holiness.
Chizkuni
מעל רגלך, “from your feet.” The reason is that you might have stepped on something unfit to be found in a holy place. The reason why the Torah added: “from your feet,” seeing we normally wear shoes on our feet, is that the word נעל also occurs for gloves, as in Ruth 4,7: שלף איש נעלו “where the translation is: נרתק יד ימינה, “sleeve of the right hand/arm.”Our sages in B’rachot 54 have ruled that no one may ascend the Temple Mount while wearing (leather) shoes. [The reason is that at a place where the reverence for the Temple prevails, it would like a lack of faith if one had to rely on shoes to be protected against snake bites, etc., instead of trusting in G-d to be protected. [I have seen this in commentary by Bartenura on Megillat Ruth. Ed.]
Rashi
MISHNA: With regard to all [items] used as monetary value for another item - items for which it is typical to give money when acquiring. At this point, we assume that [the mishna] is discussing a coin: once [the seller] gains [the coin] he is obligated [to furnish] the item being exchanged for it -- if the coin is being given under the rubric of khalipin and not under the rubric of money -- in the way that we acquire by means of a scarf, and in the sense of [the verse] "a man drew off his shoe" (Ruth 4:7).