Halloween Costume Ideas for Girls With Penis Envy

For whatever reason, when I dress up- for Halloween or not-Halloween- I like to either go as 1.) a man or 2.) a woman who dresses like a man or 3.) a crazy old woman. Dressing as someone from my own gender or my own generation just doesn’t seem like an option.

I’ve been this way ever since I was a little girl. I’m not sure what it means, but I have a feeling Freud would have a few theories on it.

So, if you’re one of those girls who likes donning a mustache and tie from time-to-time, here are some Halloween ideas to fill that itch.

This year I will be going as two of these costumes combined- Frida Mercury.

For a lot of these outfits, I would tell you to start by looking at the thrift store, but for purposes of the blog, I will share online purchases I have found.

1.) Pee-Wee Herman– The key to dressing like Pee-Wee is getting a suit one size too small. This can be very challenging as it’s often difficult for women to find a men’s two piece gray suit that is too small for her. 
Believe me, I’ve tried:
Suit– This suit I found for around $60 on Ebay. It can be tailored to different sizes. It comes from a general men’s suit wholesaler, but the seller must have had a sense of humor by pairing up the suit with a red bow-tie. This suit makes me think it’s what Pee-Wee would wear if he was cast in a James Bond movie. I found other gray suit options at Gap and Express, but they cost a pretty penny.
Bowtie– $1.49 on Amazon
Shoes– Again, I would look for these in a thrift store, but I found these on Zappos for $46.
Benetint– No PW outfit is complete without the rouged lips and cheeks- $28 (will last you forever)
Hair– As for hair, ladies, I would just try to slick it back as much as possible and draw a little widow’s peak in the front.


2.) Freddie Mercury– Who doesn’t want to be Freddie Mercury? He oozed confidence and passion and talent and wonder. He wore whatever he wanted and he got away with it. The costume belowk combines 70’s Freddie (sans mustache, longer hair) with 80’s Freddie (mustache, shorter hair):

Shiny Suspender Bodysuit–  These are 50% off at American Apparel- $18. Ladies, unless you want your ta-ta’s hanging out (which doesn’t stop the American Apparel models in the photos), you should wear a nude bodysuit underneath the suspenders.
Shiny Leggings– These are 20% off at American Apparel- $37
Buck Teeth– These puppies are $35 and pretty solid, but I’m sure you can find cheap-o ones in the Halloween store.
Chest Hair– There is something extraordinarily disturbing about that photo below. It looks like a boring merkin. Alternatively, you could just cut up hair from a wig and spirit gum it to your chest or nude bodysuit- $36
Mustache– $8.99 and well worth it…a lady should always stock up on mustaches.
Hair– Again, I would slick back as much as possible or…. I have no idea how to tell you to get that hairstyle above.


3.) Frida Kahlo- Due to polio that caused one leg to look different from the other, Kahlo wore long billowy skirts that covered her legs. Kahlo wore a lot of traditional Mexican dresses, skirts, and blouses, and rarely went without flowers in her hair:

Blouse and Skirt– Any Mexican dress or blouse and skirt should work for this. You can find them on Ebay or Etsy, but I found this one for $75 at La Mariposa Imports.
Shawl- Kahlo rarely went without a shawl as well- $48 from Frida Fashions
Hair Clip– $16 on Etsy and make sure you put your hair in a braid in the back.
Mustache– Buy two- one to put on your eyebrows and the other to wear above your lip- $8.99
Jewelry– Any over-sized and long costume jewelry should work.


4.) Annie Hall– The reigning Queen of women’s men’s fashion. Her look has always remained timeless. The key to this outfit? Confidence. Unlike Pee-Wee, you should find clothing that just a little too big for you, but not unflattering.

Vest- Again, I suggest that you just go to a thrift store for this. Any men’s vest and shirt should suffice for this outfit or- $50 at Gap.
Pants Rummage your closet for those Gap khakis you bought back in 1999 or buy new ones- $44 at Gap
Hat– A purchase that you will wear time and time again- $15.80 at Forever 21
Tie- $9.90 at Forever 21
Sunglasses– $10 at Urban Outfitters

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  • Reply Jonathan Manor October 19, 2010 at 3:31 pm

    woody allen is a pretty dumb choice.

    You already know Freddy Mercury is the best out of the best. No contest

  • Reply Melanie's Randomness October 19, 2010 at 3:34 pm

    The Annie Hall is really cute!! My boyfriend wanted to do Pee Wee but I think it would be so much awesomer if a girl did it.

  • Reply Ella October 19, 2010 at 3:41 pm

    Now, I really want to be Freddie Mercury.

    good thing I don't have a costume yet!

  • Reply Just Plain Tired October 19, 2010 at 3:57 pm

    It sounds you're going to have a well costumed Halloween. 😉

  • Reply Hipstercrite October 19, 2010 at 4:19 pm

    @Jonathan- It's not Woody Allen! It's Annie Hall!!!

    @Melanie- Pee-Wee looks great on guys and gals. You should both go as!

    @Ella- I can't wait to dress as Freddie. It's going to be so much fun. I need to go buy the mustache.

    @Just Plain Tired- Maybe I should combine all four costumes into one costume!!!

  • Reply theTsaritsa October 19, 2010 at 4:31 pm

    I was thinking of going as Hamlet this year, but my boyfriend feels uncomfortable kissing a girl dressed as a boy. Go figure.

    By the way, I thought that fake chest hair was a photo of something else…

  • Reply Jessica Druck October 19, 2010 at 5:01 pm

    amazing. i love your blog. I have never wanted to be anything slutty and this year i thought about it…then i went back to my, " i am going to wear a batman homemade boy version costume or something like it" idea

  • Reply Chantale October 19, 2010 at 5:28 pm

    I wanna do PeeWee so bad! I mean the costume, I swear… *shifty eyes*

  • Reply Meghan October 19, 2010 at 5:51 pm

    Brillz. I love being a boy. The Pee-Wee idea is amazing and I can't WAITTTT to see you as Freddie!

  • Reply Hipstercrite October 19, 2010 at 6:25 pm

    @Tsaritsa- Tell your bf to get lost and dress however you want to! 😉

    @Jessica- Ha! Love it! I'm the same way. I think that I want to be sexy, but then change my mind. One year I did both. I was Marlene Dietrich- I wore men's clothing, but had a burlesque outfit on underneath.

    @Chantale- Do him! Er….I mean…do it!

    @Meghan- What are you going as?

  • Reply Big Mark 243 October 19, 2010 at 6:27 pm

    I have never had the opportunity to dress up as a character… would not mind doing a woman, but the only person I would trust with my makeup is no longer available…

    … Jonathan is prurty slow on the draw, isn't he?

  • Reply Mademoiselle Hautemess October 19, 2010 at 6:30 pm

    Pee-Wee Herman? BWAHAHAH! Amaze-balls!

  • Reply One Blonde Girl October 19, 2010 at 10:49 pm

    Very creative. I love your costume solutions. Now if only I had somewhere to go this Halloween…

  • Reply Rahul October 19, 2010 at 11:28 pm



    /thoughts of a man

  • Reply Emily October 20, 2010 at 12:37 am

    I wish I'd thought of Pee Wee, and Annie Hall is an amazing idea.

  • Reply Jennifer Louise October 20, 2010 at 3:21 am

    Hahahahah I love this.

    I've always wanted to try Annie Hall one year.

  • Reply Z.J.Ascensio October 20, 2010 at 10:04 am

    Haha, this is great! I love how you've found all the accessories and everything! I'm linking back to in in my Ultimate Halloween Post!

  • Reply Hipstercrite October 20, 2010 at 1:23 pm

    @Mark- Who do you think you would go as?

    @Hautemess- Pee-Wee, O Pee-Wee.

    @One Blonde Girl- You don't need to go anywhere to be dressed up! Believe me, I do it all the time…

    @Rahul- HA! Your comment made me laugh out loud. I was trying to picture such a costume. However, wasn't Freddie Mercury always slutty?

    @Emily- It's a pretty easy costume to do. You should do it!

    @Jennifer- The beauty about Annie Hall's outfit is that you don't just have to wear it on Halloween!

    @Z.J. Awesome! Thanks! Can't wait to check out the post!

  • Reply Forevermelody October 20, 2010 at 6:02 pm

    Great post! I'm excited to see what you go as this year.

  • Reply Adria October 21, 2010 at 12:14 am

    Oh man! I love these ideas. I need a good idea.

  • Reply laurenne October 21, 2010 at 6:28 pm

    I LOVE going as a man too! Penis Envy for sure. I went as a tranny a year ago, and it was amazing. Big wig. Lots of makeup. Sock in pants.

    This year I was thinking Richard Simmons, but now you've got me thinking Frida. How great was that woman? I JUST saw the movie for the first time, and I'm in love.

  • Reply Polly Syllabick October 22, 2010 at 5:23 pm

    I have formerly appeared as Indian Jones, Beetlejuice and Gambit from the X-Men. I applaud your help allowing us to put gender biases and slutty variations on common themes to bed this halloween.

  • Reply Anastasia October 23, 2010 at 10:24 am

    I want to dress like Annie Hall everyday. screw Halloween.

  • Reply Cosplay January 19, 2011 at 10:31 am

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  • Reply Halloween Costumes Were Better When Moms Made Them | Hipstercrite October 26, 2011 at 8:01 pm

    […] I was a weird-ass child.” Ever since then I’ve usually gone in drag (see my post ‘Halloween Costume Ideas for Girls with Penis Envy‘) My Mom let my freak flag fly and it’s never stopped waving, but I truly miss those […]

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