Is Cross-Dressing Sinful?

woman dressed as Peter Pan

I was nervous. It was a first of many things. My first major project of my senior English class, my first time trying to teach anything on literature, my first serious tease of a satire-appreciating teacher who also happened to be related to me, and my first time in full drag.

It’s going to be a surprise for her; only my friends knew I came to school with a bag that included a wig, some simple brown flats, a long denim dress, and the rest of the components that would transform me into an approximation of our beloved teacher.

My boobs — Nerf balls — kept falling out of place as I reviewed the lesson plan I would give to the class for my project, and the dress itched in a most breezy way as I recalled recently reading Deuteronomy 22:5. “A woman must not wear men’s clothing, nor a man wear woman’s clothing, for the Lord your God detests anyone who does this” (NIV). As a new Christian, I feared I was trading God’s wrath for a gamble at a gimmick that could get me a good grade. Or not.

That didn’t help my nerves.


After my project was over, I read a harsh condemnation by the eighteenth century biblical scholar Matthew Henry. “Let stage-players and such sort of persons look to it, how they will answer to God for their continual violation of this express command; nor are those guiltless who encourage and reward such disobedience.” Based on this, God’s ire was aimed not only at me but also my fellow students and potentially my teacher, if she gave me a good grade. Not good.

Digging deeper, many years after my project, I found this verse to be tied to idolatry. St. Jerome noted that cross-dressing or transvestism’s “application is in the cultic sphere, arising from a Canaanite practice associated with a bisexual deity or from cultic prostitution involving both sexes.” The Authors of the Jamiesson Fausset Brown commentary agreed that “Disguises were assumed at certain times in heathen temples.” They cited Philacorus (as quoted by Townley in Maimonides) saying that the old Asiatics were accustomed to exchanging male and female dress when engaging in the worship of Ashtoreth.

“As elsewhere, Scripture considers the natural differences between male and female to be the Lord’s creation and so should not be disregarded or camouflaged.”
—Dr. Earl Kallard

This angle wasn’t a universally fixed line. Dr. Earl S. Kallard wrote, “The prohibition against [cross-dressing] can scarcely refer to transvestism. Though evidence for religious transvestism in ancient Canaanite religion is not conclusive, the inclusion of the rule under the proscription of things the Lord detests suggests a serious problem.” In other words, the strong language here emphasizes the point to make it clear. Kallard continues, “As elsewhere, Scripture considers the natural differences between male and female to be the Lord’s creation and so should not be disregarded or camouflaged.”

Transvestism as a Lifestyle

So did I condemn myself by seeking to achieve satire? Is my wife in sin when she borrows my coat when it’s cold out? Is it asking for the wrath of God for a young woman to play the lively role of a young Peter Pan? Or for me to attend the production and applaud?

Well, the consideration of a historical context is necessary for interpretation because the scriptural context itself is a collection of miscellaneous laws (my NIV and NASB have headings of “Various Laws” and “Sundry Laws” respectively), so the Bible itself offers no context for the verses. Yet it shows a strong emphasis, so we must be doubly certain to not dismiss it out of hand.

Personally, I believe Dr. Kallard’s comment is most insightful. The concern here isn’t a legalistic demand to restrict the wearing of pants by woman as seen commonly in China, nor the wearing of kilts by a man in Scotland. These are culturally informed perspectives subject to the audience and timing.

Rather, the issue is any attempt to blur the line between the sexes, dishonoring the very nature of God’s creation.

Basically, this verse is a clear condemnation of a lifestyle of transvestism that is purposed at confusing the gender line.

I don’t think God gave me an F back when I earned an A from a thankfully amused cousin. I don’t believe God would condemn my wife for sleeping in my boxers. I feel a man in a kilt can enjoy the breeze with an absence of conviction. I don’t think God would even be angered by a couple occasionally exchanging clothes for sexual arousal or dressing in drag for Halloween, or anything of the sort, so long as the purpose isn’t to actually live a life on the other side of a line God drew with a chromosome.

Like so much else, I believe God is concerned more with the why than the what.

Originally posted 2015-04-27 08:00:40.

Photo credit: 八木 Ricardo 清介 / Foter / CC BY
About Phil (250 Articles)
Philip Osgood is a Christian husband, father, and writer who considers himself a passable video game player, fiction reader, camping and hiking enthusiast, welder, computer guy, and fitness aficionado, though real experts in each field might just die of laughter to hear him claim it. He has been called snarky, cynical, intelligent, eccentric, creative, logical, and Steve for some reason. Phil and his beautiful wife Clara live in Texas with their children in a house with a dog but no white picket fence. He does own a titanium spork from ThinkGeek, though, so he must be alright.