Under my Kittel during Yom Kippur I wore comfortable clothes: blue jeans, non-leather tennis shoes, thick socks, and an oversized polo shirt.
I learned my lesson the hard way: teshuvah, Chabad-style, is work. Physically, emotionally, and spiritually exhausting, it is a process for which a coat, tie, and slacks are unsuited (no pun intended.) A nice suit may show respect for the holiday, but more functional attire, IMHO, shows determination, focus, and commitment.
Or so I told myself.
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