OK lil' thread on Deuteronomy 22:5, aka

"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 God your God."

Needless to say, I have some thoughts on this.

1/x thread.
First of all, a woman wearing pants is not wearing men's clothing; they are, by definition, women's clothing. Our ideas about what gender is and how it's expressed has changed a lot over the centuries, and that includes clothing.
Even leaving aside the ways our social constructions of gender have changed (women have short hair now, wear pants, etc.) like, a person in clothing is wearing their clothing.
A man in a skirt is a man wearing men's clothing. A nonbinary person in whatever the f they feel like wearing is wearing nonbinary clothing. For pete's sake.
But beyond that, how we Jews interpret this verse isn't even about crossdressing, not really.

The 11th c. commentator Rashi pushes the question further (in his commentary to Nazir 59a), arguing that the passage really intends to safeguard against adultery-- +
—that is, to prevent a woman from passing as a man to sneak into men's spaces and facilitate adulterous behavior.

The issue is deception, not gender expression.
And not just deception, but deception with the intent to bring about problematic behavior. That's what's being forbidden in Torah, Rashi argues.
Interestingly, it’s said that Rashi’s daughters wore tefillin—one assumes that this traditionally male-coded “article of clothing” (well, ritual garb) was acceptable because it facilitated piety and morality, rather than detracted from it.
So here, the question is less about what one wears and more about why one might wear it.

Expressing yourself to be more whole, more yourself, more fully you is, I believe, a true mitzvah.
And I need to say that all of us, to some degree, live in gender’s gray areas, and conscious or not, our conceptions of our own gender shifts and changes over time, as with the rest of us.
Even for folks who don't identify as trans, the clothes we choose to wear--say, nailpolish? Combat boots? Both?--can be potent tools for creating and reflecting our ever-evolving and nuanced understandings of our own genders.
(Cis ppl have gender identity and expression, too. And that might change and shift over time, even within the broad categories of "cisgender").
Torah is a guide to living in connection to God, but not an axe hanging over our necks. "You will live by them," Torah says of mitzvot. Not die by them.

So wear the clothes that help you live! Thrive! Bring joy and caring to others! Whatever that looks like!
Do what makes you whole and feel most holy and connected to the divine and yourself and other people.

Live big.

Shine bright.
This seemed so obvious to me that I didn’t even think to spell it out but ok, spelling out in case it’s helpful: https://twitter.com/grimogrelabs/status/1353401118655537154
Also! The 16th c. Jewish legal decisor the Rema says (SA OH 696:8) that crossdressing on Purim is permitted because the intention is only for joy (and not, say, facilitating harm/deception).

So if your motivation is for joy, get on with it, and feel and manifest that joy.
Exegesis is often activist in our tradition. “An eye for an eye? Obviously that means you have to pay monetary damages!” “Stone to death your rebellious kid? Obviously means [ridiculously specific thing that could never exist IRL]”. We can choose to interpret towards justice. https://twitter.com/riffchick/status/1353413655354875905
Also, like, maybe Joseph wore dresses. (Thread on the queer and the genderbendery in Joseph): https://twitter.com/theradr/status/1132668440043507712
⚔️ ⚔️⚔️⚔️⚔️⚔️⚔️⚔️ https://twitter.com/wilgafney/status/1353417031119327232
Exactly. https://twitter.com/b0wsprit/status/1353494855343861760
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