What were the Chosam, Pesil and staff that she asked for as a security?
Rashi: Chosam was his signet-ring 1 . Pesil was his cloak to cover himself.
Ramban: Pesil was his Sudar (a head-gear worn by important people over their hats) 2 and his staff was a ruler's staff. 3
Seforno: Pesil was his belt.
Ha'amek Davar: Pesil was on his outer robe. Esteemed people have it, and very esteemed people have it on the neck. Perhaps it was of Techeles, to remember Kisei ha'Kavod.
What was the significance of the items that Tamar asked for as a security?
Seforno: She asked for three personal objects 1 that symbolized Yehudah's greatness and strength. 2
Malbim: Normally, a security must be worth as much as what it is in place of; Yehudah did not have this. An esteemed person would not leave his signet ring [or staff] with someone else, so this sufficed.
Ha'amek Davar: The signet-ring hints to [Yehudah's status as] a law-maker. Pesil refers to meditation of Yir'as Shamayim, and the staff hints to a rulership (refer to 38:18:1:2 and 38:18:1:4).
Gur Aryeh (to 38:15) #1: Tamar requested items that represented Yehudah's identity fully. A man is distinct from his fellow in three aspects - a) by his personal Tzurah; 3 as represented by the signet 4 ; b) by his clothing; c) by his profession, represented by the Yehudah's staff of royalty.
Gur Aryeh (to 38:15) #2: A person bears children for three motives - a) so that his name not be erased; b) to create more 'branches' in his family (even if he has children already); c) to rely upon in old age. By asking for these three specific items, 5 Tamar was indicating that her entire intent in being with Yehudah was to have children from him, and not for Zenus.
Gur Aryeh (to 38:15) #3: Tamar was hinting to Yehudah that there were three reasons that he should marry her - a) so that the name of the deceased not be erased; 6 b) For Yehudah himself, for he had but one son remaining, and had not yet fulfilled Peru u'Revu; c) for Tamar, so she would have children to rely upon in old age. 7
Seforno: About which she concentrated her thoughts during their intimacy (so that she would have children like him). Refer to 38:18:3:1.
In the expression of Maharal, Tzurah means form-defined function. Refer to 22:5:151:2*.
Gur Aryeh: The same way a person's handwritten signature testifies as to the person who signed it.
Gur Aryeh: She asked for - a) Yehudah's Chosam, for a child is a signature signed by the father (see the parallel in Yeshayahu 8:1,3 - CS). b) for his Tzitzis. Just as the Tzitzis is an outgrowth that emerges from the garment, a child emerges from the parents' Guf (which is itself but a garment for the Neshamah) The term Anaf (branch) also relates to Tzitzis. c) his staff, symbolizing reliance in old age.
According to Gur Aryeh; this union was a fulfilment of Yibum prior to Matan Torah. Refer to 38:16:1.1:3.
The meaning of these three items is as explained above, in the note to the previous answer.
Why does the Torah add the word "Lo" (after "va'Tahar")?
Rashi: To teach us that the twins with whom she was pregnant would be strong like Yehudah, and righteous like Yehudah. 1
Ha'amek Davar: She was indebted to him to establish seed for the deceased.
Refer to 38:18:2:1**.
QUESTIONS ON RASHI
Rashi writes that "Pesilecha" was his cloak. If so, it should have said 'Simlascha'! And surely Yehudah did not leave without clothing!
For other interpretations of "Pesilecha," refer to 38:18:1:2 and on.
Mizrachi: 'His garment to cover himself' hints to the Mitzvah of Tzitzis - "Kesusecha Asher Techaseh Bah" (Devarim 22:12). Perhaps it was a small scarf, and he was properly covered even without it. Gur Aryeh - The word Simlascha would imply all his garments. It writes Pesilecha; he gave to Tamar the [additional] garment he wore to fulfill the Mitzvah of Tzitzis; that is why it is called Pesilecha ('your fringe'). 1
Gur Aryeh: As for the Ramban's astonishment that Yehudah would disgrace his Tzitzis by giving them to a harlot; a) as above, she was no longer a harlot, but rather designated for Yehudah alone; b) Chazal teach that the Hashem sent the Mal'ach appointed over Ta'avah (desire) to Yehudah, causing him to act against his better judgement.