Crossdressing as marilyn monroe

You can almost feel the anticipation. It comes but once a year. It’s the time when crossdressers can express their true selves without fear of ridicule. So it’s time to glam up!

Last year at Halloween time I wrote a post describing some of the many crossdresser halloween costumes that men can choose from during this season. I thought this year I’d share some more of my favorite costumes and inspire you to take a bold step out crossdressed this year!

Who doesn’t want to look as glamorous as Marilyn Monroe in her heyday? When you crossdress as Marilyn you’ll get to dress to the nines and show off your flirty side. As an added bonus, you can coordinate this costume with your loved one, who has the choice of many public figures who had steamy relationships with Marilyn.

After years of trying to convince my wife to go as a sexy school girl, I figure that perhaps she wants me to lead by example 🙂 If you decide to crossdress as a schoolgirl this Halloween, be warned. This costume will require a feminine physique to pull off well. If you’re looking for a school girl costume a bit more forgiving of the male figure, try this still sexy yet less revealing schoolgirl costume.

Halloween Crossdressing Advice

A few things to keep in mind when you’re out crossdressed this Halloween. The most important thing is to have fun! Don’t worry what people will think, everyone is dressed up. Don’t worry about being too feminine – you can just say you’re getting into character. If you’ve nervous of revealing your secret, don’t dress in everyday woman’s clothes! The more backstory you can provide about your costume, the safer you’ll be. Having to explain why you just happen to have the perfect matching blouse and skirt could be…interesting.

Trick or treat!


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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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Noni Simone
Noni Simone
12 years ago

I’ll have to find the African-american equivalent….Marilyn doesn’t really work for a African-american girl……lol

Ces4200' class='avatar avatar-64 photo' height='64' width='64' />
12 years ago

I just love this time of year,

Vanessa Law
Vanessa Law
12 years ago
Reply to  Ces4200

hehe – definitely a great time to let your inner woman out without fear!

Felishia Lopez
Felishia Lopez
6 years ago

I’m really looking forward to chatting and making friends, I’ve been dressing up since I was about 5 years old when my mom and her cousin thought it was cute but then she stopped but I really liked it and wanted to continue so I have been dressing up since I was about 10 years old on my own but doing it secretly I want to just come out so bad but I am afraid to, I have been dressing up and going out in public about 7 times but only at night and have been with several men and… Read more »

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