Why is Kesusoh written with a Hei?
Moshav Zekenim: This teaches that if the borrower owes a hundred and his garment is worth two hundred, we do not tell him to sell it and buy an inferior one worth a hundred, and give the creditor the hundred in payment of his debt. 1
R. Shimshon Refa'el Hirsh: The feminine shows that we should feel his weak, downtrodden state.
See Torah Temimah, who learns this from the word "Simlaso", which implies an expensive garment. Moshav Zekenim: However, nowadays we rule like R. Tam, that we do not leave a creditor with what he needs.
Having specified the top and the under-garments, why does the Pasuk continue "be'Meh Yishkav"?
Rashi and Targum Yonasan: To include the leather bedspread.
Mechilta: "Kesuso... Simlaso le'Oro ba'Meh Yishkav" includes all Keilim. 1
Hadar Zekenim: I command you to return it to him, for in what will he lie?!
It is not clear however, why the Torah needs to mention all three, (EC)
What are the connotations of "ve'Shama'ati ki Chanun Ani"?
Ramban: It teaches us that if someone cries out to Hashem with all his heart, Hashem listens to his cries, even if he is not worthy. 1
Rashbam and Riva citing R..M. of Kutzi: Strictly speaking, the creditor has a security (which he owns). His obligation to return it is Lifnim mi'Shuras ha'Din (beyond the letter of the law), in which case, when the creditor fails to return it, Hashem ought to ignore his cries. And it is only because Hashem is gracious that He answers him. 2
Seforno: Even though the poor man has no basic claim against you, since he borrowed from you and owes you money, Hashem will listen to his cries because you left him without clothes, following which He will deduct part of the extra money with which He graced you to provide others less fortunate than yourself, and give it to him. 3
Moshav Zekenim #1: I (Hashem) am gracious. Also you should be gracious and go beyond the letter of the law, and return his security!
Moshav Zekenim citing R. Asher: Do not say, I will not take [for a security] a Tzadik's garment, but I will take a Rasha's garment. I (Hashem) am gracious, and I hear the cries of everyone!
Moshav Zekenim #2, Da'as Zekenim #1, Hadar Zekenim #1: When the Oni will scream 4 to Me about the good that I did to him - "v'Shachav b'Simlaso u'Veracheka", I will hear him, and bless you.
Hadar Zekenim #2: I (Hashem) am gracious, and I do not want you to pressure him too much. If you want to collect from him based on the letter of the law, also I will collect when you are liable to Me! 5
Mechilta: 'I created the world with Midas ha'Rachamim (and you should take your cue from Me'). 6
Because 'Chanun' is a derivative of the word 'Chinam', implying that when one supplicates to Hashem, He responds with a Matnas Chinam, irrespective of one's credentials (See also Rashi at the beginning of Va'eschanan).
Rashbam and Riva: As opposed to Pasuk 22, in connection with an Almanah and a Yasom, where the Torah does not use the Lashon "Chanun" - because they are crying out to Hashem min ha'Din.
You are therefore well-advised to return him the security in its time, thereby ensuring that Hashem continues to grace you with the extra money to continue providing those in need.
Hadar Zekenim, Da'as Zekenim: The Oni's cry is 'I was created in Your form like him - he lies in comfort in his bed, and I do not have what to lie in!' However, this is difficult, for we do not find "Chanun" for evil.
See Torah Temimah, who elaborates.
QUESTIONS ON RASHI
Rashi writes that here we discuss a day garment, Why does it say "ba'Meh Yishkav"?
Moshav Zekenim: The previous verse teaches a day garment, and here it teaches a night garment. Even though (Devarim 24:13) "Hashev... v'Shachav b'Simlaso" teaches a night garment, that is needed to teach that the lender acquires the security - "u'Lecha Tihyeh Tzedakah."