Royal Garments (לבוש מלכות): The Knesses HaGedolah cited in the Elyah Rabbah (Orach Chaim, 696:15) writes that the reason we dress up is to remember the miracle in the Purim story where the wheels turned for our favor, when, ויצא מרדכי מלפני המלך בלבוש מלכות תכלת וחור ועטרת זהב גדולה ותכריך בוץ וארגמן והעיר שושן צהלה ושמחה, the moment when Mordechai was taken around on the horse dressed in royal garments. This miracle was particularly special, because at first he wore sackcloth and ashes, and later he wore magnificent royal garments. (According to this reasoning, it’s implicit in the Eliyah Rabbah that one should dress up in beautiful royal garments, and not in the clothes of poor people.)
Tail: The Elyah Rabbah (696:15) offers another reason, which is that we dress up to remember the downfall of queen Vashti. The Medrash relates that she refused to come in front of Achashveirosh because she had grown a tail, and this was the beginning of the salvation which led to Esther becoming the queen. (According to this reason, perhaps one should specifically dress up like an animal that has a tail.)
Internally We Are Good: The Bnei Yissoschar (Ma’amorei Chodesh Adar, Ma’amer 9, ois 1) brings in the name of the Maharam Chagiz “a nice insight to simply explain the custom”. The Gemara (Megillah 12a) relates that Klal Yisrael were worthy of annihilation as they bowed down to the image (tzelem) in the days of Nevuchadnezzar. However, they merited a miracle כי השתחוו רק כלפי חוץ – “they only bowed down outwardly,” i.e. inside they believed in the Ribbono Shel Olam, and only externally did they pretend to believe in another God. Since they only served avodah zorah outwardly, the decree against them was only outwardly.
Based on this, on Purim we cover over our faces and change our clothing so that we look like goyim, to show that although on the outside we may look like goyim, that is only externally, however, in truth, on the inside we are G-d fearing and wholesome Jews. And the same thing is every time a Yid unfortunately sins and acts like a non-Jew, it is only externally, however, inside we are G-d fearing and wholesome Jews.
Purim is a Holiday of Concealing (Hester Panim): Purim is in truth a hidden holiday. On the outside, it was a string of coincidences which saved the Jews – Achashveirosh’s choice of Esther as queen, Mordechai’s overhearing the plot to assassinate the king, Achashveirosh’s insomnia just before Haman arrived to request Mordechai’s hanging, etc. In fact, G-d’s name does not even appear in the entire Megillah. Yet behind the scenes, it was the Hand of G-d which truly brought about the salvation. Those discerning enough to perceive it recognized G-d behind the veils – and understood that even when the world appears to function as normal, following chance and the laws of nature, it is truly G-d who is in control. Therefore, just as G-d was hidden during the Purim story yet in truth present, we hide ourselves behind our masks and costumes while we celebrate the salvation. In doing so, we remind ourselves that the world is not what it appears on the outside. Rather, the outside world is nothing more than a façade obscuring the true power of G-d behind it. (Ta’amei Minhagim 892)
To Remember the Non-Jews Who Dressed Up Like Jews (מתיהדים): In Megillas Esther (8:17) we learn: רבים מעמי הארץ מתיהדים – “Many of the people of the land became Jewish.” The Pirush HaGra (Esther 8:17) says that people of the land weren’t sincere coverts, and they feigned Jewishness in order to curry favor with the Jews. Based on this some explain that we dress up, to show that just like they pretended to be someone they weren’t, so too we dress up and pretend to be someone that we are not.
This concept highlights the Purim miracle, as originally, they tried to wipe out all the Jews, and suddenly everything flipped around, and it changed so much to the extent that the enemies of the Jews, wanted to be like the Jews.
Masks in the Megillah: The Shu”t Knesses Yechezkel explains that we dress up with masks to remember the numerous people in the Megillah who wore masks so to speak: 1) Malach Gavriel covered over the appearance of Vashti and made her a tail (Megillah 12b), so that she would be too ashamed to appear before king Achashveirosh. 2) Esther so to speak wore a mask over her face, as she hid her origin, and withheld the fact that she was Jewish, so that everyone would think she was one of them (Megillah 7a). 3) Malachei HaShores disguised themselves as Haman’s son’s and cut down trees in the garden of Achashveirosh and explained that Haman commanded them to. 4) Eliyahu HaNavi dressed up as Charvonah and said to Achashveirosh (Esther 7:9), “The tree which Haman made for Mordechai, is good for the king”, as mentioned in Pirkei D’Rabbi Eliezer (Perek 50) and Yalkut (1059).
Reversal (ונהפוך): Some explain that we dress up on Purim to highlight the idea of ונהפוך הוא – “Everything was reversed” (Esther 9:1), which is the main theme of what happened in the Purim story. The Jews went from a helpless minority threatened with annihilation to a favored class, granted carte blanche to destroy their enemies. Wearing costumes – which entirely transform a person's looks – reflects the Jews' utter transformation – from victim to victor.
Remembrance of Amalek: Another reason written in Yalkut Me’am Lo’ez (Esther pg. 267), the Ketzos HaShulchan (end of Vol. 3) and in Shu”t Siach Yitzchak (siman 380) is to remember the downfall of Amalek, who changed their clothes when they came to fight with Klal Yisrael on their way to the land of Eretz Yisrael, yet, Klal Yisrael still managed to defeat them. We also find in Tosfos (Rosh Hashanah, daf 3) and in Rashi (Bamidbar 21:1) that in the times of Shaul HaMelech, the Amalekim turned themselves into animals with the use of sorcery, and the same thing in the times of Yehoshofat.
Purim Gelt [Money]: Some suggest a practical reason. Purim is a special day for giving tzedokah. The Gemara writes that we give to “anyone who sticks his hand out” – without inquiring how needy the person actually is (Bava Metzia 78b). Thus, since the poor – and even people who would rather not become known as paupers – would be especially active going out collecting on Purim, the custom arose for them to wear masks to hide their identity and preserve their dignity (Minhag Yisrael Torah (Hilchos Megillah) quoting the sefer Minhagei Kol Torah; Sichos Chachamim, pg. 30; Shu”t Mishneh Halachos 3:60; Sefer Purim V’Chodesh Adar, of R’ Tzvi Cohen pg. 94; Sefer Ginas Bisan and Sefer Otzar HaMinhagim)
National Unity: One of the key elements which brought about the Purim salvation was unity. Haman threatened the Jews because he saw them as a nation “scattered and dispersed” among Achashveirosh’s kingdom (Esther 3:8). The Jews were contentious and disunited, many compromising their Jewishness in order to blend in with whichever one of Persia’s 127 provinces in which they lived. And as separate and isolated individuals, they were quite vulnerable to the threats of the great masses which sought to destroy them. In response, Esther said to “gather all the Jews” (4:16)– to bring them together, as a single nation, united in G-d’s service. We too wear costumes to hide our individuality. Nobody knows who’s inside a gorilla costume. By doing so, we obscure our separateness and individuality – and become a united nation.
Stealing the Birthright: Another reason mentioned by the Sefer HaToda’ah (Perek 10) is that Amalek hated Klal Yisrael because Yaakov stole the berachos from Eisav, when dressing up like him. We dress up to show that this wasn’t falsehood and trickery and that we deserve to get Eisav’s inheritance. The Sefer HaToda’ah writes: Both Jew’s and non-Jew’s disguise themselves; Eisav shows himself to be righteous and meticulous, and inside he is wicked. Tzadikim on the other hand such as David – appear to be sinners, but inside are pious, Yaakov – although he was a tzadik he hid it, to the extent that Yitzchak didn’t even feel that he merited the berachos.
עד דלא ידע: The Sefer HaToda’ah writes that another reason for dressing up is based on the concept that Chazal (Megillah 7b) bring of עד דלא ידע – until one doesn’t know. Since we find this concept on Purim, we dress up and that way people don’t know who we are.
To Scare: The Mishnah (Shabbos 66a) teaches that one isn’t allowed to go out wearing לוקטמין, on Shabbos. The Gemara explains that לוקטמין refers to something known as פרמי, and Rashi explains this to mean “an item that one ties on his face to scare children.” The word פרמי is similar to the word Purim, and this is a smach [reliance] for the custom of wearing face masks on Purim.
The Prohibition of “Lo Yilbash”
The Shulchan Aruch (Yoreh Deah 182:5) rules that it is forbidden for a man to wear a woman’s garment or vice versa, and even one item of clothing, such as a woman’s hat on a man, or a woman’s shoe on a man is a problem, even though the identity of the wearer is evident from the other items of clothing that he/she is wearing. As it says in the pasuk (Devorim 22:5):לא יהיה כלי גבר על אשה, ולא ילבש גבר שמלת אשה - “There shall be no man’s garment on a woman, and a man shall not wear a woman’s garment.”
What Age Does the Issur Start?
The Shu”t Igros Moshe (Even HaEzer 4:62) writes that the age for when a child needs to start being worried about dressing modestly is the age that the parents are particular to dress the child in gender appropriate clothing. And if the child understands what is being put on him, then there is mitzvah of chinuch to ensure that the child dresses appropriately
Is There a Heter of “Lo Yilbash” On Purim?
There is dispute amongst the Kadmonim by simchas Purim and simchas nissuin if there is room to be lenient with the prohibitions of “lo yilbash” and “shatnez”. According to the Mahari Mintz (siman 15) and ruled by the Rema (Orach Chaim 696:8) it is permissible for a man to wear a woman's garment, and for a woman to wear a man's garment. According to this reasoning, the Darkei Moshe (siman 696) also permits dressing up with costumes which contain shatnez that is normally forbidden on a rabbinic level.
The Heter Is Based on Three Reasons:
1) The Gemara in Avodah Zorah (29a) allows a man to look in the mirror if he doesn’t do it with the intent of beautify himself, and the prohibition of “lo yilbash” is only when it is being done for beauty (see Tosfos who speaks this out).
2) Tosfos Acherim (Avodah Zorah 29a) brings that if men are accustomed to looking in mirrors like women, then doing so is no longer prohibited, as it can’t be considered a “women’s garment”.
3) The Riva allowed bochurim to snatch food due to simchas Purim, from the time we start reading Megillah until the end of the Purim seudah (two nights, and one day). Surely doing so is considered theft? We see that due to simchas Purim we are lenient. Therefore, we can learn from here that there is room to be lenient with “lo yilbash” and “shatnez” as well.
Some say that based on the third heter, there is only room to be lenient on Purim itself, and not on the days before and after Purim. However, some say even during these days there is room for leniency, as in the end of the day it is being done because of simchas Purim.
Strong Opposition
The Knesses HaGedolah (Orach Chaim 696); Darkei Moshe (Orach Chaim 696) based on the Mahari Brin (although the Darkei Moshe himself concludes it’s permissible) and the Bach (Yoreh Deah 182) based on the Yeraim (siman 385, 386) don’t allow violating “lo yilbash” or “shatnez derabonon” due to simchas Purim and snatching food is an exception based on the principle of hefker beis din hefker, the principle that beis din have the ability to relinquish one’s ownership over his property and give it to someone else.
The Taz (Yoreh De’ah 182:4) and Be’er HaGoleh (Yoreh Deah 182) both write that according to strict halachah it may be allowed, however, the correct thing is to try and nullify this custom.
The Aruch HaShulchan (696:12) writes that the custom is not to do this anymore, as we aren’t on the level to be able to do such things.
The Mishnah Berurah (696:30) after bringing the Taz and Be’er HaGolah writes in the name of the Pri MeGodim that if it’s recognizable that one is a man, as he is wearing just one item of woman’s clothing, אפשר שאין למחות בהם – “perhaps there is no need to protest.”
Room for Stringency Regarding Shatnez
In regard to wearing shatnez, there is more room for concern as in the end of the day the one wearing the costume derives benefit from it (שכן נהנה) and R’ Akiva Eiger (Shu”t siman 8) writes that by shatnez we apply the rule of שכן נהנה, i.e. if in the end of the day one derives benefit from the item, he violates the prohibition.
We find this concept primarily by חלבים ועריות – forbidden fats, and forbidden relationships, and R’ Akiva Eiger applies it to shatnez as well.
Children
According to the Steipler zt”l (Orchos Rabbeinu, Vol. 3, ois 105-107) it is forbidden to wear even one female item of clothing on Purim, however, there is room for leniency for a young child who has not yet reached the age of chinuch. One of the Chazon Ish’s relatives (cited in Dinim V’Hanhagos, Perek 22, ois 10) once came to visit him on Purim with his daughter who was 4/5 years old and she was wearing trousers (pants). the Chazon Ish got very angry and said, “Is this chinuch?” Some allow girls to dress up when they are among their friends and not on the street, however, this is provided that it is clear that it is being done for the purposes of dressing up.
Davening Whilst Wearing a Costume
From the Shulchan Aruch (Orach Chaim 91:5) it is clear that when davening one should be dressed in clothing that are suitable to stand in front of the king with. Does this mean that davening whilst wearing a costume is a problem? Another point worth considering before davening in a costume, is that it is likely to distract other people who are davening.
Poskim Who Say That It Is Forbidden
According to R’ Elyashiv zt”l (Yevakshu MiPihu, Purim Vol. 2, Sha’ar 8, Perek 1, sif 9) one shouldn’t daven whilst wearing a costume, if one wouldn’t stand in front of a king in such a manner. According to R’ Chaim Kanievsky zt”l (Alei Siach, Orach Chaim pg. 214, Osicha pg. 307) and R’ Nissim Karelitz zt”l (Nesivos Halachah, Purim pg. 205 and 216) it is not appropriate, and if possible, one should wear regular clothes.
Poskim Who Allow
The Shu”t Si’ach Nochum (43) writes that the general custom is to daven with a costume, as on the day of Purim it is fitting to stand in front of great people with such attire.
R’ Shmuel HaLevi Wosner zt”l (Shu”t Shevet HaLevi 10:18:1) writes that a chosid dressed up as a litvak, and vice versa is okay.
R’ Yosef Dov Septimus shlita (Igeres HaPurim, Perek 6, he’orah 13, pg. 42) is medayek from the Shevet HaLevi that if the costume one is wearing is not respectful then it is a problem. R’ Yehuda Cheznar shlita (Sha’arei Yemei HaPurim pg. 57) also writes that strange clothing is prohibited. In Kovetz MiBeis HaLevi (Inyonei Chanukah Purim, Kislev 5766, pg. 42, he’orah 26) they bring this clearly in the name of R’ Wosner and they write: “I heard from the Shevet HaLevi, that he doesn’t mean to allow costumes that are extremely funny, such as a monkey etc.”
According to R’ Mordechai Gross shlita (Nekiyus V’Kavod B’Tefillah pg. 151) one may daven wearing a mask as the Rema mentions wearing it on Purim, however, regarding a costume, it needs more examination. On other hand, the Shu”t Mechakrei Eretz (Vol. 3, Orach Chaim 91) writes that a costume is allowed, however, a mask is a problem. The difference is, a mask is easy to remove, however, a body costume requires more effort, and there is more room to be lenient.
Hesech HaDa’as [Distractions]
Is it permissible to daven in front of a person wearing a costume that has pictures on it? The Rema (Orach Chaim 90:23) writes, “It is forbidden to draw pictures in seforim that one davens from, as it can be distracting.” Based on this the Mishnah Berurah (s.k. 71) brings in the name of the Magen Avraham not to paint paintings on the walls of shul’s on a level that catches people’s eyes, as it can be distracting. Based on the above, there is room to question if one is able to daven facing someone who is wearing a distracting costume.
Is It Permissible to Dress Up Using a Tallis and a Kittel?
R’ Zilberstein (Chasukei Chemed 26b) discuses if one is allowed to dress up using a kittel. Initially he writes that seemingly it would be forbidden as we find in Yoma (23b): בגדים שנשתמשת בהן קדושה חמורה תשתמש בהן קדושה קלה – “Would you consider using a garment that was used for a very holy act, for a less holy act?” Therefore, in regard to a kittel as well, a kittel is used for davening on Yomim Noraim, it has kedusha, and one is forbidden to take it into the beis hakisay as is clear from Mishnah Berurah (610:18), and since we find that it has kedusha, how could one use it for his Purim costume?
However, he then writes that seemingly it would be permitted, as bigdei kehunah are items used for kedusha (תשמיש דקדושה), whereas a kittel is only used for a mitzvah (תשמיש מצוה) and it’s clear from the Gemara in Megillah (26b) that items used for a mitzvah may be thrown away, whereas items used for acts of kedusha require genizah [special burial], we see that items used for a mitzvah aren’t as kadosh. Meikar hadin [strictly speaking] one may take a kittel into the beis hakisay as is clear in the Mishnah Berurah (8, s.k. 37) in regard to a tallis, and the din of kittel is like that of a tallis as is clear in Mishnah Berurah (21, s.k. 14) therefore, it comes out, that one may dress up using a tallis and a kittel.
She’hechayanu on a New Purim Costume
If one buys himself a new expensive Purim costume, and he is very excited about wearing it, should he recite the berachah of she’hechayanu?
R’ Chaim Kaniesvky zt”l (cited in Mo’adei HaGrach) held that one should recite she’hechayanu, even if he is wearing it for just one day. The sefer VeZois HaBerachah (pg. 315) brings that according to R’ Elyashiv it needs to be both expensive and exciting for the one wearing it. The sefer Gam Ani Odcha (R’ Gamliel Rabinovitz, Orach Chaim 141) writes that min hadin one may recite she’hechayanu, however, if he is worried about making a berachah levatolah, he should have kavonah during she’hechayanu of Megillah that it goes on the costume as well.
Summary
Dressing Up: On Purim the minhag Yisrael is to dress up with masks and a variety of colorful clothing. Primarily it is done to increase joy on the day of Purim. In addition to the above reason, the seforim bring down numerous other reasons.
“Lo Yilbash”: There is a machlokes Rishonim if on Purim there is a heter for a man to dress up as a woman and vice versa. Some are lenient as it is being done for simcha, and some forbid. If one is lenient and changes just some of his items of clothing to that of the opposite gender, we can’t protest. Some are lenient with children that are not yet of the age of chinuch.
Going in the Ways of Goyim: It is permissible to dress up using a tallis and kittel, one may also dress up as a clown, goy, Haman and Achashveirosh. However, it is not appropriate to dress up as a negative character. It is forbidden to dress up as a priest.
Costumes for Davening: Some poskim strictly forbid wearing costumes during davening. Some allow it if it is a dignified appearance worthy of standing before the king. Some distinguish between a mask and a costume.
(The above write-up on Purim costumes was largely based on gilyon Oimek HaPeshat #153)
Dressing Up as a Non-Jew or Priest
In regard to dressing up like a non-Jew, such as Haman or Achashveirosh, R’ Chaim Kanievsky zt”l held that it is not a problem of ובחקתיהם – “Going in the ways of the non-Jews.”
In regard to dressing up like a priest etc. according to R’ Chaim Palagi zt”l (Ruach Chaim, Yoreh Deah 178:2) one shouldn’t stand in front of the amud with such a costume.
According to R’ Elyashiv zt”l (Ashrei HaIsh, Vol. 3, Perek 48, ois 6) it is forbidden to dress up as a priest and the like, due the prohibition of: ושם אלהים אחרים לא תזכירו לא ישמע על פייך – "The names of other God’s you shall not mention, nor shall they be heard from your mouth."