Halloween 2009 is only a few days away, have you decided on whether or not to dress up? If you’re having a little bit of trouble deciding what to be, there is plenty of inspiration out there. Princess, Hooter’s girl, Wonder Woman and She Devil are all popular costumes for crossdressers during this time of year.
Of course, there’s always the option to simply go en femme to your Halloween gathering, just you as you normally crossdress. However, if you’re looking to spice things up a bit and really freak people out, you can opt for a mish mash of characters, read on to see what I’ve cooked up.
5. Serial Killer French Maid
You’ll Need – A french maid’s outfit that can be found at any costume shop and a toy knife.
Your Character Motivation
This is a classic crossdressing outfit, especially appealing to those who are into role reversal.
Just like in the board game Clue, the maid did it. You are a psychopath freshly escaped from the county insane asylum and your looking for your next victim. With a feather duster in one hand and your weapon of choice in the other, you rampage through the town, leaving cadavers and immaculately clean homes in your wake.
4. Skeleton Cheerleader
You’ll Need – Surprisingly enough, cheerleading outfits can be found at your local thrift store for dirt cheap. If you can’t find one there, most costume shops also carry them. Be sure to pick up skeleton makeup as well.
Your Character Motivation
You cheered loudly for your squad and fired up the crowd during every home game, that is until the town was cursed. The conservative school administrators used to accuse you of showing too much skin and now you don’t show any! Go! Team! Scare!
3. Frankenhooker
You’ll need – A wig and a sexy hooker outfit e.g., lingerie, a short skirt and stiletto heels. A frankenstein’s monster makeup kit and perhaps some metal objects to use as neck bolts.
Your Character Motivation
Okay, I have to admit that this is not my idea but rather the plot of a 1990 Horror Comedy directed by Frank Henenlotter. The mad scientist Jeffrey Franken loses his fiance to a horrible accident and decides to bring her back to life using body parts from various local prostitutes. She soon goes crazy and runs wild in the city.
2. Vampire School Girl
You’ll need – Fangs and a catholic school girl outfit from a thrift store or a costume shop.
Your Character Motivation
You’re the girl who’ll do anything for an A and that includes drinking your teacher’s blood and granting him or her immortality in exchange for a good grade.
1. Zombie Bride
You’ll need – A wedding dress, fake blood, monster makeup kit and some raw meat (optional)
Your Character Motivation
You loved every bit of your husband — especially his brain! Widowed by your own cravings, you now roam the Earth in search of another hunk …. of human flesh! A woman’s wedding day is the most important day of her life and all eyes are on her — in this case literally! Okay, enough zombie puns
, you get the idea.
I hope that you enjoyed this list. What is your craziest crossdresser costume idea and have you followed through on that idea? Leave a comment below and Happy Halloween!

{ 10 comments… read them below or add one }
I’m actually going to a costume part tonight as a hooters girl. I bought a ridiculously large pair of fake breasts to wear uner an actual official uniform. Of course, the club i go to i’m always dressed up anyway so it’s no real stretch for me. Just larger than normal breasts.
Cool, sounds like fun Kendra
Simply awesome. I’m seriously considering the vampire schoolgirl!
Cool, Kristi! Let me know if you do
That’s so spooky – no pun intended. For some reason I was thinking about the Frankenhooker film. Don’t ask why, my mind’s all over the place
Hehe, I haven’t seen the film yet but I want to
I go to the thrift stores all the time and cheer leader outfits are one rare item. Maybe I could go as a boy and shock myself? You do have some great ideas. Strange how on halloween one can dress up any way we want and no one cares but any other time ,our social awareness comes into play. Can we declare a 365 day Halloween awareness idea to the general public.
Thanks, Leslee.
That is a cool thing about Halloween, you can literally dress up or down as anyone or anything and nobody will really judge you.
I wore of course a traditional black witches dress Conical hat .Carried a broomstick Long black No mask. But really heavy make up red red lipstick Black Mascara Black eyebrows and red eyeliner Really ugly over done make Such fun frightening little boys and girls. They thought I was really a witch ?. Most did not recognise me Who have seen me as Joanna many times
Blessed Be
Hi Jessica
I just loved the list…… I just wish you had been able to find someone to model each outfit.
Halloween is just picking up over here in the UK, but unfortunately it never especially had a cross-dressing aspect to it. Maybe that will change, but too late for me!!
Hugs
TinaCortina xx
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