Gender, Drag, and Six-Inch Boots: Syd’s Big Experiment

What does gender mean to you? For Syd Young, answering that question meant diving headfirst into something completely out of their comfort zone—drag. Think six-inch white leather boots, burlesque classes, and a whole lot of trial and error.

“I had no idea if hyper-femininity was for me,” Syd admits. “But I knew I had to find out. What would it feel like if I chose it?”

Over 10 months, Syd explored everything from lap dancing to walking in heels, uncovering not just what femininity meant to them but also how freeing it could feel to let go of the rules altogether. This is the story of how one big experiment turned into a journey of self-discovery—and why the answers aren’t always as important as the questions.

This is the story of how one big experiment turned into a journey of self-discovery—and how you can start exploring what gender means to you, too.

What Even Is Femininity?

“Honestly, femininity always felt like something other people decided for me,” Syd says. “I played tennis, so I had to wear skirts. I wore a dress to my college graduation because that’s what people expected. But none of it ever felt me. It felt like I was just checking boxes for other people.”

Sound familiar? That’s because femininity (and masculinity, for that matter) is often handed to us like some one-size-fits-all outfit. Spoiler: it doesn’t fit everyone. For some, femininity might mean long hair and high heels. For others, it’s an attitude, a feeling, or something entirely different.

So Syd started asking the big question: “What would femininity feel like if I got to choose it?”

Syd Tried Drag—And Everything Changed

To answer that question, Syd dove headfirst into drag. Over 10 months, they went on a crash course in hyper-femininity, complete with burlesque lessons, pole dancing, and learning how to walk in heels without falling over (harder than it looks, apparently).

“I went all in,” Syd says, grinning. “We’re talking thigh-high white leather boots, long blonde wigs, and routines that made me move in ways I’d never even tried before.”

But the best part? Syd didn’t do it alone. Their drag mentor, Alexander the Great, is a trans man, and their choreographer and backup dancers, Zoja and Nix, are nonbinary. Together, they created an environment where Syd could experiment and explore without fear of judgment.

“It wasn’t just about the clothes or the choreography,” Syd explains. “It was about feeling safe to try something new. That made all the difference.”

What Syd Learned About Gender

Here’s the thing: after 10 months of drag, Syd realized hyper-femininity wasn’t for them.

“I loved the experience, but heels and long hair? Definitely not my thing,” Syd says, laughing. “But what I did learn is that femininity doesn’t have to look a certain way. It’s not about anyone else’s definition—it’s about finding what works for you.”

And maybe the biggest takeaway? Gender isn’t some neat little box. “For a long time, I thought I had to pick a side—either super masculine or super feminine. But gender is way more fluid than that. It’s not about picking a label; it’s about exploring what feels good and letting yourself evolve.”

So, How Do You Explore Gender?

Not everyone’s going to take up drag (though Syd highly recommends it if you’re curious). But there are plenty of ways to dip your toes—or heels—into exploring gender:

• Start Small: Try on different clothes, hairstyles, or makeup at home. Thrift stores are great for finding fun, affordable pieces to play around with.
• Find Your People: Having a supportive community makes everything easier. Whether it’s friends, a local group, or even an online space, finding people who get it is a game-changer.
• Be Curious: Gender isn’t all-or-nothing. It’s okay to try something, decide it’s not for you, and move on. It’s all part of the journey.
• Go Slow: There’s no rush to figure it all out. Take your time and enjoy the process.

The Journey Never Really Ends

At the end of the day, figuring out gender—or any part of who you are—isn’t about reaching some final destination. As Syd puts it:

“I’ve come to the belief that the journey is never really over. We don’t hit a point where it’s all figured out. We’re constantly evolving and becoming the most true version of ourselves.”

And that’s the beauty of it. Whether you’re just starting out, deep in exploration, or somewhere in between, there’s no rush and no wrong way to do it.