The high school I graduated from (and work at now!) has opposite sex day each year for the seniors. The guys wear dresses, the girls dress like men and put on fake beards.
The year I was a senior our student council decided not to because it would be politically incorrect. :rolleyes:
I have done this once as a practical joke. When I was younger and still lived at home my sister and I looked very much alike. She had long blonde hair, but still had a blonde fall wig for some odd reason and when I put it on one night, the resemblance was incredible. My father had not come home yet, so we decided to pull one over on him. I put on the fall and dressed up in my sisters clothes and sat in his armchair and waited.
After he came home I was there for at least 15 minutes before he realized who I actually was.
I’ve been known to steal my dad’s sweaters and shirts.
points at first link in sig
As a man, I’m a niche market item. I consider it a public service not to dress as a woman.
I did wind up wearing my wife’s jeans for a day, but that was a “getting dressed in the dark” problem rather than a decision.
I’m an amateur, but small-time multiple award-winning, Drag King.
Crossdressing woman here. Did myself up as an old Jewish man for a play I was in. Mustache, bushy eyebrows. It rocked!
As for men in drag…I’ve done a couple up. One was for a play, another for Halloween.
I made fast friends with some Drag Queens and Transvestites during the years I spent frequenting gay clubs. And I’ve been to many many many drag shows.
I want to open up a school for drag queens. Some just really need help. I still think that is my true calling…
As a grad student teaching an undergrad course on “Sociology of Deviance”, I bought myself a denim wrap-around skirt. The only thing making it “women’s clothes” is tradition and culture (it fit nicely and in no way made me look female), but there’s definitely a dearth of skirt-wearing males, generally speaking. So I rode the LIRR in it, walked across campus in it, attended various courses wearing it, went to the city dump to pick up our house’s designated recycling container while wearing it, and, uh… :o …went to the bank to make a deposit and, as I normally would, stepped over the little velvet ropes that create the queue line because there was almost no one else there…good thing because when I did so I pulled down the chain of velvet ropes :o yeah, skirts are cool and comfy and I would wear one more often if part of me wasn’t on edge in case of problematic fallout, BUT there are some things best done in pants and stepping over velvet bank queue-line ropes is among them.
So I did this off and on and then showed up for one of my classes dressed that way after issuing the assignment to my class that they were to do something that was not illegal and not harmful but definitely deviant in the sense of violating social norms and report on their experiences.
Got a round of applause and some whistles when I showed up 
Well, duh. Berkeley. You could dress as a trout and not get any odd looks.
I had a cross dressing roommate. He pulled it off rather well. IIRC it started out as a halloween thing and I think he enjoyed it so much it became a lifestyle choice.
It’s an interesting sub-culture that you don’t hear so much about (other than the posterchild movies Pricilla Queen of the Desert and To Wong Foo, Thanks for Everything, Julie Newmar – both good, but Pricilla is better.)
We went to a couple of his shindigs, I remember meeting an ABSOLUTELY STUNNING tall, stacked, woman there. She was wearing a skin tight black lycra thing, the makeup and hair was fabulous. The Illusion was PERFECT right up til ‘she’ shook my hand. You can’t disguise man hands.
There’s also a certain cross section of CD’s that haven’t ‘come out’ fully. (repercussions, etc.) It’s, um, wierd seeing a guy with a pink low back frock and a bunch of back hair.
The funny thing is, there’ s a whole spectrum to it. At the low end, wearing women’s shoes around the house, and at the other end post-op sexual reassignment. (I’ve heard from said roomate that the surgery is VERY good, if you catch my drift.)
I don’t dress in drag but I used to work with a guy who dressed up in drag. Alan was a hilarious gay guy, kept us all laughing though he was a whiner too. His drag persona was this jewish woman named Ida. Brought pictures one day, and when I left for college he warned me if I got into trouble he’d send Ida after me.
Does being in a Rocky Horror cast count? If it does I’ve dressed in drag a lot.
Give me some men who are Crossdressing Men
who will fight for the right to wear frocks.
Start me with ten, who are Crossdressing Men
and we’ll learn how to tuck in our — Oh!
Shoulder to shoulder we flirt and we smoulder
Though we wear pumps with white socks!
Then—there’s nothing in the world can bag or run our hose,
When—Crossdressing Men—can walk around in Wifey’s clothes!