The Shulchan Arukh states that the right shoe should be put on first, but the left shoe should be tied first. Last week we gave one explanation: wearing clothes, and particularly shoes, represents strengthening and protection; tying represents binding or restraint. The right side, representing mercy, is particularly in need of strength and protection; the left, representing judgment, is in need of moderation and restraint.
This explanation should apply to any kind of tying, and this is logical since the principle itself is learned from the fact that we tie the tefillin on the left hand. And indeed the Kitzur Shulchan Arukh states explicitly that we should tie the left side first on all kinds of garments. (KSA 3:4.)
However, the Mishna Berura rules that precedence to the left applies only to leather shoes. Even shoes, if they are made of fabric, need not be tied on the left first (MB 2:6). Why should tying the left apply specifically to shoes? To understand this approach, we have to go back to Rebbe Yochanan’s original statement which is the source for tying the left first, according to the passage in Shabbat (61a): “Shoes are likened to tefillin”.
What is the likeness between shoes and tefillin? Last week we explained that both are tied. But the Levush, an early Acharon who is the source for the Mishna Berura, gives a different explanation: The gemara states that in the merit of Avraham’s statement that he would not accept from the king of Sodom “from a string to a shoe lace” (Bereshit 14:23), his children merited two mitzvot: the thread of techelet in the tzitzit, and the straps of the tefillin (Chullin 89a). According to this, the likeness of tefillin is specifically to shoe laces, not to other kinds of tying. And as we have mentioned many times, “shoes” in halakha generally refer to leather shoes only. (It is also clear that the likeness is not due to tying alone, because from the continuation of the passage we see that the reward includes the straps of the head tefillin.)
We can elucidate this explanation with the help of another approach we have often used in explaining the symbolism of shoes, an approach elaborated in the writings of Rav Natan of Breslav. Shoes represent our physical possessions; our property gives us dignity and elevates and protects us from the hazards of the natural world, just as our shoes dignify us, elevate us, and protect us from cold, dampness, sharp pebbles, and so on. Mankind’s first private possession was the “suits of leather” given Adam and Chava by G^d; Rav Natan writes that these were leather shoes.
This applies particularly to leather, because leather shoes exemplify mankind’s ascendancy over animals. This ascendancy was in need of clarification immediately after the sin of Adam and Chava, which eroded it and in some ways reduced us to the level of beasts – for example, by making our food “the herb of the field”(Bereshit 3:18). (This clarification was continued in the story of Kayin and Hevel. Kayin thought that mankind was closely akin to the animals; he expressed this sentiment through excessive mercy, when he refused to bring animal sacrifices, and then through cruelty, in the bestial act of killing his brother.)
Shoelaces, by extension, represent being tied and attached to our possessions. While being attached to our possessions is natural and to some extent unavoidable, it doesn’t embody our highest nature. Ideally we would like our possessions to aid us in G^d’s service, but without having them bind and constrain us; we don’t like being slaves to our property. So we tie our shoes first on the left side, which is the less important and dignified side, to show that this attachment is an unfortunate necessity.
Avraham Avinu resisted the temptation to be subordinated to material wealth; he declined the offer of the King of Sodom to give him the spoil of war. Avraham knew that this would make him beholden to the King of Sodom, and he gives as the reason of his refusal that he doesn’t want the King to be able to boast, “I enriched Avram” (Bereshit 14:23). We follow in Avraham’s footsteps, and reject excessive attachment to our possessions by tying the left shoe before the right.