Str8Curious is a monthly AskMen column where out and proud lifestyle expert Joey Skladany answers burning questions from heterosexual men about sex, dating, and the LGBTQ+ community. No topic is off limits as he candidly lends advice, debunks stereotypes, and gives it to you straight — err — gay. Should you be interested in submitting a question for editorial consideration (and we will respect anonymity), feel free to ping Joey directly on Instagram or email him at joeyskladanywrites@gmail.com).
The Question
“I’m a straight and cisgender man, yet I’ve had a sudden desire to dress up in drag. I have no clue where it stems from but I like the idea of completely transforming my appearance and getting in touch with my feminine side. Where do I even begin and how do I ensure that I’m not doing it in an offensive way?” – Rodney, Portland, OR
The Answer
One of my favorite RuPaul quotes is “We’re all born naked and the rest is drag.”
Whether it’s a three-piece suit, a frilly dress, or a hodgepodge of thrifted items from Goodwill, clothes are an expression of personal style and an extension of how we want the world to perceive us.
But sometimes we yearn to bend the rules and experiment with outfits that defy gender “norms” and conformity. And that’s entirely okay! The most dynamic and complex humans don’t attract attention by playing things safe — they creatively, boldly, and confidently explore their identities while not giving two effs about what others may think of them.
So first and foremost, kudos to you for having an open mind and a willingness to explore this side of yourself. Some of the best episodes of Drag Race feature heterosexual men trying drag during makeover challenges and they, perhaps more than any special guest on the show, embody their female personas wholeheartedly and completely transform into these characters.
It’s simply human instinct (and fun!) to play roles that are different from our everyday lives.
My first bit of advice is to start by experimenting behind closed doors. If you’re scared of shopping for clothing, makeup, and accessories in person, order them online for easy and discreet delivery. This will allow for you to get a better sense of how you feel while wearing said get-up and seeing yourself in the mirror for the first time.
Second, drag isn’t inherently offensive unless your intention is to make a mockery of specific people. And even this approach has a gray area, as imitation of noteworthy figures can often be considered art or a form of flattery. But if anything you’re doing feels like you’re poking fun at or stereotyping women in general, especially those who are trans, err on the side of caution and simply don’t go there.
While some might see Halloween as a good first-time opportunity to lean into girlhood, it has its drawbacks, too.
While there is a comfort in knowing that everyone around you is also dressed up, it still may limit the ability to really tap into a side of yourself that you’ve put on the back burner for so long, as people will see your costume as just something you’ve done for the holiday, rather than an exploration or expression of self.
That being said, if you think wading into this slowly is the right approach for you, maybe starting with a fun Halloween costume is the way to do it.
RELATED: What Your Halloween Costume Says About You
When it comes to the look itself, there are plenty of YouTube tutorials that detail the process of getting into drag, from makeup tips and wig styling sessions to tutorials on walking in heels and tucking (the act of taping genitals to give the illusion of having a vagina).
And while it may be your instinct to simply ask a local queen for help, please keep in mind that drag is not only an artistic expression, but also a career. These ladies will expect some type of compensation for their time and you should be ready and willing to fork over some cash to support them
RELATED: Why You Should Appreciate Drag Queen Culture
Once you’ve given it a go, get in tune with your emotions. Do you feel more confident? More beautiful? More empathetic to the struggles that women face before they get ready for a night on the town?
If drag is something you want to dabble in occasionally, that’s fine! If it’s something you want to pursue more frequently and potentially in a public setting, search for amateur drag nights at your local gay bar and sign up. The community should be nothing short of supportive as you start this journey that is—dare I say—fabulous.
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The Question
“I’m a straight and cisgender man, yet I’ve had a sudden desire to dress up in drag. I have no clue where it stems from but I like the idea of completely transforming my appearance and getting in touch with my feminine side. Where do I even begin and how do I ensure that I’m not doing it in an offensive way?” – Rodney, Portland, OR
The Answer
One of my favorite RuPaul quotes is “We’re all born naked and the rest is drag.”
Whether it’s a three-piece suit, a frilly dress, or a hodgepodge of thrifted items from Goodwill, clothes are an expression of personal style and an extension of how we want the world to perceive us.
But sometimes we yearn to bend the rules and experiment with outfits that defy gender “norms” and conformity. And that’s entirely okay! The most dynamic and complex humans don’t attract attention by playing things safe — they creatively, boldly, and confidently explore their identities while not giving two effs about what others may think of them.
So first and foremost, kudos to you for having an open mind and a willingness to explore this side of yourself. Some of the best episodes of Drag Race feature heterosexual men trying drag during makeover challenges and they, perhaps more than any special guest on the show, embody their female personas wholeheartedly and completely transform into these characters.
It’s simply human instinct (and fun!) to play roles that are different from our everyday lives.
My first bit of advice is to start by experimenting behind closed doors. If you’re scared of shopping for clothing, makeup, and accessories in person, order them online for easy and discreet delivery. This will allow for you to get a better sense of how you feel while wearing said get-up and seeing yourself in the mirror for the first time.
Second, drag isn’t inherently offensive unless your intention is to make a mockery of specific people. And even this approach has a gray area, as imitation of noteworthy figures can often be considered art or a form of flattery. But if anything you’re doing feels like you’re poking fun at or stereotyping women in general, especially those who are trans, err on the side of caution and simply don’t go there.
While some might see Halloween as a good first-time opportunity to lean into girlhood, it has its drawbacks, too.
While there is a comfort in knowing that everyone around you is also dressed up, it still may limit the ability to really tap into a side of yourself that you’ve put on the back burner for so long, as people will see your costume as just something you’ve done for the holiday, rather than an exploration or expression of self.
That being said, if you think wading into this slowly is the right approach for you, maybe starting with a fun Halloween costume is the way to do it.
RELATED: What Your Halloween Costume Says About You
When it comes to the look itself, there are plenty of YouTube tutorials that detail the process of getting into drag, from makeup tips and wig styling sessions to tutorials on walking in heels and tucking (the act of taping genitals to give the illusion of having a vagina).
And while it may be your instinct to simply ask a local queen for help, please keep in mind that drag is not only an artistic expression, but also a career. These ladies will expect some type of compensation for their time and you should be ready and willing to fork over some cash to support them
RELATED: Why You Should Appreciate Drag Queen Culture
Once you’ve given it a go, get in tune with your emotions. Do you feel more confident? More beautiful? More empathetic to the struggles that women face before they get ready for a night on the town?
If drag is something you want to dabble in occasionally, that’s fine! If it’s something you want to pursue more frequently and potentially in a public setting, search for amateur drag nights at your local gay bar and sign up. The community should be nothing short of supportive as you start this journey that is—dare I say—fabulous.
You Might Also Dig:
Str8Curious: Gay Sex & Dating Slang, Explained Str8Curious: Common Questions About Gay Guys, Answered Str8Curious: How to Make a Profile for a Gay Online Dating App