It is an extra pious act to commence all things with one’s right side, because the Torah ascribes more importance to a person’s right side (as was in the Temple when sprinkling oil on a lepers’ right thumb and big toe). According to Kabbalah, ‘right’ signifies grace and compassion, while ‘left’ signifies judgment and law, and with our actions, we should augment grace over judgment. Therefore, those who observe the extra pious custom are strict to eat with their right hands. Additionally, for washing and applying creams, one’s right side precedes his left. When washing one’s entire body, a person should first wash his head and then wash his right side. Also when dressing, it is an extra pious act to begin with the right sleeve, and do the same with pants and socks. When removing one’s clothes, one should start with the left side.
Concerning shoes, the law is more complex. On the one hand, one should begin with the right side. On the other hand, we learn from the commandment to tie tefillin on one’s left arm, that for all matters involving tying, one is to start with the left side. Therefore, one first puts on his right and then left shoe, without tying them, and when tying the laces, he starts with the left and then ties the right (Shabbat 61a; Shulchan Aruch 2:4).
A person who is left-handed starts with his right side, both for putting on his shoes and tying the laces.
The objective of this halachah is to ensure that every deed we do, even such a mundane act as putting on our shoes, is done as precisely as possible. For indeed, people put on their shoes every day, so why not learn to do it in the most perfect way? Certainly, one who accidentally mixes up the sequence need not take off his shoes in order to put them on again in the appropriate order. With these halachot, Chazal teach us to attribute value to every act we perform, along with their details, thereby helping us to grasp the profundities of the actions that make up our lives.