How to Cross-Dress this Halloween

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There are many Halloween costume options.
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As every child figures out within the first few years of trick-or-treating, Halloween is the perfect time to step out of your day-to-day life and try on a new identity. One way to do this is through cross-dressing Halloween costumes, which can offer a safe way for people of any gender to explore different gender identities and types of gender performance.

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Why Cross-dress for Halloween?

Gender binary and gender determinism are so prominent in our day-to-day lives that even people who feel comfortable in their assigned gender may want an escape every now and then. Just as it can be fun to dress up as a vampire or a wizard and pretend that you possess supernatural powers, going cross-dressed at Halloween can let you walk in someone else's shoes — literally.

For some folks, though, the opportunity to dress up as another gender is more than a fun escape from reality. It's a way to try on a reality that's previously been hard to access or completely unavailable due to social and other pressures. For some trans and gender-nonconforming folks, Halloween is an early refuge in their journey of gender discovery.

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Choosing a Halloween Costume

On a holiday where everyone is trying to look like something or someone they're not, it's easy to dress as another gender and see how it feels without the people around you asking a lot of questions that you may not be prepared to answer just yet. There are a number of cross-dressing ideas out there, so as long as you find one that's respectful and with which you're comfortable, you should feel free to go for it.

If you're just trying to avoid the aggressively gendered marketing of many professional Halloween costumes, there are lots of choices for costumes designed for any gender. From costume ideas for single partiers, duos and groups to great costumes that aren't specific to any one gender, there's truly something for everyone.

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Masculine-Coded Costumes

Are you wondering how to cross-dress for Halloween if you want to try dressing in a way that's traditionally masculine-coded? Look up Halloween costume ideas for men and see what jumps out at you. To flatten out breasts if desired, you can wear a tight-fitting sports bra or look into options for binders. You can dress comfortably in men's clothing when you're unaccustomed to wearing them if you do your research or check out cross-dressing tutorials.

Many Halloween or costume stores sell fake beards and different kinds of facial hair that can be affixed to the face using spirit gum. If you have longer hair that you typically wear down, check out a tutorial for creating a faux-pixie haircut, which allows you to simulate short hair. Alternatively, you can pin up your hair under a hat.

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Feminine-Coded Costumes

If you want to dress and style yourself in a more traditionally feminine way, YouTube tutorials for different hair and makeup choices abound. Costume stores sell cheap wigs that are often pre-styled. If you already have long hair, hair gel and bobby pins can work wonders to get the style you want. Makeup needs will vary depending on your costume, but a simple application of concealer, lipstick, eye liner and mascara can produce a dramatic change without breaking the bank.

To simulate breasts, you can buy a cheap bra and stuff it with socks, pantyhose filled with rice or breast forms (prosthetics). You can also try using shapewear to smooth out bumps and create the illusion of curves as desired.

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When buying clothing designed and marketed for women, remember that clothing sizes vary widely among stores and brands. Men's pants come in standard, measurable sizes, but women's pants (and shirts and dresses) are different at every store. The same is true of Halloween costumes, so try before you buy if possible.

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