How to Enjoy and Celebrate Halloween as a Crossdresser

Ah, yes, Halloween¹ It has always been one of my favorite seasons. A nice aesthetic, candies, tricks, and of course the costumes. I’ve always loved the idea of crossdressing during Halloween because the possibilities are almost endless! Halloween itself is a wonderful opportunity for crossdressers to express themselves. They can dress in a more feminine way, almost free of judgment. You may also find out that it’s the perfect excuse for some experimentation.

If you are to crossdress or cosplay in public during Halloween, you are only limited by your own imagination. However, keep in mind that each outfit may suit a specific purpose, and they work very differently in each situation. This way, before you decide which outfit is the best for you, you need to understand better how you want to be seen this Halloween.

1. How do you want to present yourself

Well, I believe this is one of the most important questions you need to ask yourself. Do you prefer to show yourself as a crossdresser? A man dressed in a female costume for fun? Or do you want to pass as a woman in a women’s costume? Crossdressing during Halloween is something society is more susceptible to accept. So, either way you’ll be somewhat safe and less likely to get stares. In the worst scenario, you can always use the “It’s just a costume” excuse.

Keep in mind that if you want to pass, you’ll need to spend more money and time, but the results are way more rewarding. But If you want to dress up in a female costume and make it obvious that you’re a crossdresser, you’ll have less work to do. However, don’t expect a very convincing result or to be treated like a woman right away. If you want to pass, but don’t think you’ll be able to, try it anyway! It’s worth a shot, and you can be surprised by the results.

If you want a bit more realism, practice your skills and train your mannerisms. Practice is your best ally. We have about a month plus a couple of weeks before Halloween, so the sooner you start practicing, the higher your chances of passing are. Use this time to practice makeup skills, train your voice and get used to wearing shapewear for a longer time. It both improves your skills and boosts your confidence and morale. Training your shapewear resistance, voice and body language is something very important. Especially if it’s your first time crossdressing in public. When we crossdress at home, we rarely pay attention to this kind of detail, but they make a lot of difference when we are outside. Here’s an article that can improve your feminine deportment

On the other hand, if you want to dress up for fun, you’ll have a lot less to worry about. You can be yourself and socialize with other people wearing what makes you comfortable. In that case, you won’t need to emulate feminine behavior. This is very personal for each crossdresser, so take your time to think. With time, you’ll figure out how you want to experience your crossdressing Halloween.

2. The costume

This is the most interesting part, to say the least, since choosing a costume can be lots of fun. It’s an opportunity for you to cosplay as your favorite female characters, try out new outfits or just a general excuse to crossdress in public. Trying to look like a specific character tends to be a bit more demanding and expensive, but the other two options are also great.

To better represent the Halloween theme, I would like to recommend goth makeup and a dark outfit. Corsets and fishnet tights are also spot-on for Halloween. Another bold, yet pretty common approach, is to simply dress up as a woman and say that’s your costume. I wouldn’t recommend this last one, since it can be offensive for some people, and it strays from the spirit of Halloween.

One problem you may find is that female costumes in Halloween stores tend to be over-sexualized. It’s hard to find something different from costumes labeled “sexy witch” or “sexy cop”, or at least something that properly fits in a male body. That’s why I recommend you make your own costumes or order a custom-made one in your size. However, if you want to embrace the cliche and dress up as a “sexy something”, i have a few tips for you. Get yourself some breast forms and paddings and use a corset to gain some curves. As you’ll be wearing them for a long time, get a corset that doesn’t compress your waist too much.

Give preference to breast forms that are unlikely to fall off your chest! My go-to forms for this kind of situation are the vest-like breastplates from Roanyer.

3. Tips on how to make your own costume

I love to make my own costumes and cosplays! DIY (Do it yourself) costumes are great to exercise your creativity, but they also allow you to try out new approaches. You can go beyond the run-of-the-mill costumes and do something really wonderful. If you want to try it out yourself and impress your friends, I have a few tips to share.

● The materials

The materials, of course, may vary according to what you are planning on doing. Also, complex materials are better bought than made, such as wigs, lenses, shapewear and breast forms. But I can recommend some essential items that are almost always going to be used. Some of them are hot glue, silver tape, painting brushes, EVA foam, Velcro and spray varnish.

● Armory

Some costumes may include armors, swords and other stuff. I, for example, am planning on making myself a Bo-Katan costume, from Star Wars, for this Halloween.

EVA foam, cardboard and Sintra plastic are great materials for this kind of costume, as they are easy to cut and mold. Velcro is very useful to attach the pieces of your armor, and hot glue to reinforce joints. Here is a video can tell you how to make armors.

● Dresses and other outfits

If you are good at sewing, try to make your own feminine costumes out of fabric.

Lots of templates are available online for different costumes, and you can resize them to fit you. My tip is to use a piece of cheaper fabric since you can purchase more of it and do some tests. If you have enough confidence, you can go straight to the high-quality stuff, but you’ll have to take care and avoid making mistakes. If you struggle to find something in a color you need, try dying some white fabric! As a last resort, you can buy one. The following video will show you how to make a Tudor Witch costume.

● The makeup

For most costumes, you can simply do your usual crossdressing makeup, if it’s convincing enough. However, for Halloween, it’s recommended for you to add a scary tone to it. You can draw spiders and webs hanging from your eyeliner, or a few bats flying above it. Purple, red and black are spot-on tones for eyeshadow and lipstick, and fake blood can be poured on your mouth for a vampiresque look. Here is a video that can tell you how to makeup for Halloween.

4. About comfort

Remember what I said about wearing your outfits for too long? Well, with that in mind, comfort plays a key role in your wellbeing and on how long you can take it. What I have to say is that you shouldn’t wear something that turns crossdressing into a challenge.

Avoid any shapewear that hurts you, and dress for the weather in your region, so you can enjoy your night out. Otherwise, you might feel uncomfortable and tired too early, and that can ruin your Halloween. This article has some recommended stores for crossdressers to buy corsets.

5. Where to go

For most crossdressers like us, the good old trick or treating may seem to be a little boring. Halloween parties are rather common, and if you’re lucky enough, you already have an invite. If that’s not the case, try to meet new people (or even new crossdressers) online, and ask them to go out with you. If you are out as a crossdresser, tell your plans to your friends, and they might arrange something. Bars and pubs are also an option, but I wouldn’t recommend going alone, since you don’t know how strangers would react to a crossdresser.

One of the best parts of Halloween is that you can surprise your friends. You can show up as a girl even if you aren’t out as a crossdresser and see their reactions. That surely would be a story to tell. This is, of course, better if you have a group of friends to hang out with, but you can have some fun by yourself too.

If you do pass well enough as a girl, you can try those open parties by yourself, but it would still be a bit risky if you don’t. You can also stroll through your neighborhood, go on a date (why not?) or even stay home giving away candy to some trick-or-treaters. It’s all up to you, how confident you are and what makes you comfortable.

As we can see, Halloween is the paradise of crossdressers. It’s not everyday that we see an opportunity to go out as a girl and enjoy the company of friends and familiars. We can try out new outfits, practice our skills and surprise our friends, as long as we feel comfortable with it. After all, we are supposed to have fun and be ourselves on this day!