(א) בָּרוּךְ אַתָּה יְהֹוָה אֱלֹהֵֽינוּ מֶֽלֶךְ הָעוֹלָם אֲשֶׁר קִדְּ֒שָֽׁנוּ בְּמִצְוֹתָיו וְצִוָּנוּ לַעֲסֹק בְּדִבְרֵי תוֹרָה:
(1) Blessed are You, Adonoy our God, Ruler of the Universe, Who sanctified us with commandments and commanded us to be engrossed in the words of Torah.
From Rabbi Benay Lappe and Dan Libenson, "A Third Torah From Sinai: Revising Our Myth for a New Jewish Era, https://svara.org/hot-off-the-shtender-a-third-torah-from-sinai-revising-our-myth-for-a-new-jewish-era/
God gave Moses three torahs at Mount Sinai—the written torah, the oral torah, and the svara torah—the torah of our own moral intuition, the torah that is in our hearts and minds, the torah that we know to be True in our kishkes, the torah drawn from the insights gained from our lived life experiences—and the queerer the lived life experience, the richer the insight, and the more essential it is to be brought into the tradition which so desperately needs it in order to be the liberatory enterprise it has always sought to be.
(27) And God created human in Their image, in the image of God They created them; male and female They created them.
(7) Hashem our God formed man from the dust of the earth. They blew into his nostrils the breath of life, and man became a living being.
(20) And the man gave names to all the cattle and to the birds of the sky and to all the wild beasts; but for Adam no fitting helper was found. (21) So Hashem our God cast a deep sleep upon the man; and, while he slept, They took one of his ribs and closed up the flesh at that spot. (22) And Hashem our God fashioned the rib that They had taken from the man into a woman; and They brought her to the man. (23) Then the man said, “This one at last is bone of my bones and flesh of my flesh. This one shall be called Woman, For from man was she taken.”
By Rabbi Elliot Kukla and Rabbi Rueben Zellman, "Transgender 101: Gender Diversity in Judaism", https://www.keshetonline.org/resources/transgender-101-gender-diversity-in-judiasm/
The Mishna and the Talmud (the earliest forms of Jewish law and folklore, which were compiled between the first and the seventh centuries) extensively explore the role of exceptionally gendered individuals in Jewish society. In addition to ish and isha, man and woman, our Sages identify four other genders. There is the andgrogynos, a person with both male and female sexual characteristics. The tumtum, a person with neither fully developed male or female genitals. The ay’lonit is a person who was assigned female gender at birth, but developed male characteristics during maturation. The saris, is a person who is assigned male gender at birth but lacks male genitals (either since birth or due to a medical intervention.) The midrash (in Bereshit Rabah) posits that Adam, the first human being, was actually an androgynos. While in the Babylonian Talmud (Yevamot 64a) the radical claim is made that Abraham and Sarah were tumtumim, people with indeterminate gender.
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(א) ויאמר אלקים נעשה אדם בצלמנו כדמותנו. אמר רבי ירמיה בן אלעזר: בשעה שברא הקדוש ברוך הוא את אדם הראשון, אנדרוגינוס בראו, הדא הוא דכתיב: זכר ונקבה בראם. אמר רבי שמואל בר נחמן: בשעה שברא הקב"ה את אדם הראשון, דיו פרצופים בראו ונסרו ועשאו גביים, גב לכאן וגב לכאן. איתיבון ליה, והכתיב: ויקח אחת מצלעותיו?! אמר להון: מתרין סטרוהי, היך מה דאת אמר: (שמות כו): ולצלע המשכן, דמתרגמינן ולסטר משכנא וגו |
And God said: Let us make Adam in our image, as our likeness: R' Yirmiyah ben Elazar said, when Hashem created the First Adam, they were created as both genders; thus is it written, "male and female did Hashem create them." R' Shmuel bar Nachman said, when Hashem created The First Adam, God created them with two faces, one on each side, and [when God made Eve,] God split them along the middle, forming two backs.
[His students] challenged him: but it is written, "And [God] took one of his ribs!" He said to them, ["mitzalosav" doesn't mean rib, but] one of his sides, like that which is said, "and to the 'tzela' of the Mishkan," which is translated "the side of the Mishkan."
By Joy Ladin, "Torah in Transition", http://www.transtorah.org/PDFs/Torah-In-Transition.pdf
But convenient as it has been, the “male and female God created them” model doesn’t allow for the possibility of transition. I might be able to look male or female, but according to the binary template, I could only, absolutely, be one or the other. Some of us may be created according to the male and female binary; I wasn’t. Like Adam, I’m a homemade creature. God didn’t create me in relation to a category; I had to be individually imagined, assembled, animated. Like Adam, I had to confront the loneliness of that individuality before I could find my place in the world, and like Adam, I have learned that what I needed to find that place was always within me
A woman must not put on man’s apparel, nor shall a man wear woman’s clothing; for whoever does these things is abhorrent to Hashem your God.
כי תועבת FOR [ALL THAT DO SO ARE] AN ABOMINATION [UNTO THE LORD THY GOD] — This implies that the Torah forbids only the wearing of a garb that leads to abomination (adultery) (cf. Sifrei Devarim 226:1).
By Rabbi David Teutsch, "Understanding Transgender Issues in Jewish Ethics", https://www.reconstructingjudaism.org/article/understanding-transgender-issues-jewish-ethics
The Talmud says that what is prohibited is falsifying identity for the purpose of spying on the other sex. The great medieval commentator Rashi says that the prohibition is limited to concealing identity for the purpose of adultery. The Shulhan Arukh notes that cross-dressing is permitted on Purim because its purpose is simha (celebration, joy) and that it is forbidden if it is for the purpose of fraud. In limiting the prohibition to situations of fraud and deception, the talmudic and medieval rabbis indicated that [dressing] in a way that is true to the [individual's] identity is permitted.
It is permitted to get married on Purim. Rama: This refers to both the fourteenth and the fifteenth of the month, and one can certainly perform Pidyon Haben too. As to the custom of wearing 'faces' on Purim, and men who wear women's dresses and women wearing men's attire - this is not forbidden, for they have no intention other than pure pleasure. So too the practice of wearing kilayim, rabinically forbidden mixtures of clothes. And although some say it is forbidden, we follow the first opinion. So too, the custom of stealing from each other in a happy way - this does not fall under the prohibition of 'Do not steal', and this is what is done, as long as one does not transgress what is considered acceptable by the elders of the town.
From Rabbis Elliot Kukla and Rueben Zellman, "To Wear is Human To Live – Divine (Parashat Ki Teitze)", https://www.keshetonline.org/resources/to-wear-is-human-to-live-divine-parashat-ki-teitze/
Each and every soul is created in the multifaceted image of the Creator. When we try to conceal that uniqueness, we cause ourselves pain. And when we ask others to obscure themselves, we cause harm to them. The great majority of [parashah Ki Teitze] is concerned with the minute details of preventing harm. The lines before our verse teach that if we see that someone’s donkey has fallen down, we are required to help that person lift the animal up. The verse immediately following instructs us never to hurt a mother bird as we are collecting her eggs. And the very next verse commands us to build a guardrail, or parapet, around the roof of our houses, to prevent anyone from falling off. The verse about what to wear is nestled amongst mitzvot that guide us towards exquisite levels of empathy and gentleness towards all of creation.
(ו) כִּ֣י יִקָּרֵ֣א קַן־צִפּ֣וֹר ׀ לְפָנֶ֡יךָ בַּדֶּ֜רֶךְ בְּכׇל־עֵ֣ץ ׀ א֣וֹ עַל־הָאָ֗רֶץ אֶפְרֹחִים֙ א֣וֹ בֵיצִ֔ים וְהָאֵ֤ם רֹבֶ֙צֶת֙ עַל־הָֽאֶפְרֹחִ֔ים א֖וֹ עַל־הַבֵּיצִ֑ים לֹא־תִקַּ֥ח הָאֵ֖ם עַל־הַבָּנִֽים׃ (ז) שַׁלֵּ֤חַ תְּשַׁלַּח֙ אֶת־הָאֵ֔ם וְאֶת־הַבָּנִ֖ים תִּֽקַּֽח־לָ֑ךְ לְמַ֙עַן֙ יִ֣יטַב לָ֔ךְ וְהַאֲרַכְתָּ֖ יָמִֽים׃ {ס} (ח) כִּ֤י תִבְנֶה֙ בַּ֣יִת חָדָ֔שׁ וְעָשִׂ֥יתָ מַעֲקֶ֖ה לְגַגֶּ֑ךָ וְלֹֽא־תָשִׂ֤ים דָּמִים֙ בְּבֵיתֶ֔ךָ כִּֽי־יִפֹּ֥ל הַנֹּפֵ֖ל מִמֶּֽנּוּ׃
By Rabbi Mike Moskowitz, "I'm a Boy and These Are My Clothes", https://jewishweek.timesofisrael.com/im-a-boy-and-these-are-my-clothes/
Gender identity and sexual identity are different, independent, and critical to distinguish in conversations about Jewish law and tradition. For those who choose to shut down conversations about these issues by quoting Scripture, Deuteronomy 22:5 is to gender expression what Leviticus 18:22 is to homosexuality. The verse states: “A man’s garment shall not be on a woman, nor shall a man wear a woman’s garment, for anyone who does so is an abomination of Hashem.” But as I understand it, this verse is the very source that not only permits transgender Jews to wear clothing that supports their gender identity, but also arguably obligates them in doing so.
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By rejecting the right of transgender Jews to wear clothing that most supports their gender identity in religious spaces, it is not only a communal failure of our responsibility to provide sanctuary for all of G-d’s children, but also a denial of the truth of the Torah itself.
By Rabbis Elliot Kukla and Rueben Zellman, "TransTexts: Cross-Dressing and Drag", https://www.keshetonline.org/resources/transtexts-cross-dressing-and-drag/#meaning
We can flip mainstream understandings of our verse on their head and understand it as a positive mitzvah: a sacred obligation to present the fullness of our gender as authentically as possible. Unfortunately, not everyone is able to fulfill this mitzvah without endangering their life or livelihood, and the protection of human life always comes first in Judaism, but the Torah wants us be able to be true to ourselves.