Lost in the shuffle of planning Dragon Con and my upcoming Japan trip is a milestone that completely snuck up on me.
A special anniversary. No, not a relationship anniversary…well, not in the traditional sense anyway.
This year marks 15 years since I started cosplaying regularly, which is honestly wild to think about. Somehow a decade and a half has gone by since I decided to jump headfirst into one of the most fun, chaotic, and occasionally wallet-destroying hobbies out there.
Now, if we’re being technically accurate, my first cosplay moment actually happened back in 2008. My anime club put together a Super Smash Bros. skit for the Anime Expo 2008 Masquerade, and I played Ike. Not only was it my first time in cosplay, but our group ended up winning Best in Show, which is still one of those “did that really just happen?” moments looking back on it, especially since said performance was done in front of what I heard was about 5000 people in the Peacock Theater (then called the Nokia Theater). If you’re curious what that looked like, here’s the actual Masquerade performance:
Anime Expo 2008 Masquerade – our Super Smash Bros. skit that won Best in Show.
But even after that, cosplay wasn’t something I immediately kept doing. The main reason was simple: cosplay isn’t cheap. Between costumes, wigs, props, and everything else associated with the hobby, it adds up fast. Even though hobbies are fun and provide memories and new friendships, it was something I just couldn’t justify doing it regularly at the time.
It wasn’t until 2011 that I finally started cosplaying consistently. And when I did, I decided to try something a little outside my comfort zone. I decided to try crossplay.
For anyone unfamiliar with the term, crossplay is when you cosplay as a character of a different gender than your own. It’s a style of cosplay you’ll see a lot at anime conventions, but it definitely comes with its own unique learning curve.

One of my earlier crossplay attempts: Yui from K-ON .
For starters, there was the whole “I am a very hairy person attempting to cosplay anime girls” situation.
That led to my introduction to the magical—and slightly terrifying—world of Veet and Nair. If you’ve never used hair removal cream before, the experience can basically be summarized as: apply mysterious chemical paste and hope you didn’t leave it on too long.
Let’s just say there was some trial and error involved before I figured out what actually worked.
Then there was cosplay sizing, which is often a gamble—especially when ordering from overseas shops which I imagine is where a lot of people buy their cosplay if they aren’t making it or having it commissioned. I definitely had a few early costumes where my first thought was something along the lines of, “There is absolutely no way this is fitting.” and “How did they get my measurement so wrong?”
After a couple of those experiences, I adopted a very important rule:
Only buy from places where I can submit measurements. Even then, I’ve adopted the practice of adding a little padding to my measurements. I would much rather deal with something slightly loose which can easily be altered than discover I’ve ordered a costume that fits like it was made for someone half my size and I’ve just wasted money
Some people solve this problem by learning how to sew.
I admire those people greatly.
I am not one of those people.
Sewing requires a level of patience that I’ve come to accept I simply do not have. I know myself and my temper well enough to realize that if I tried to build everything from scratch, most projects would probably end up abandoned halfway through. So instead I’ve fully embraced my role as a cosplay buyer and assembler and focus my energy on the parts of cosplay I actually enjoy.
Then there are wigs.
Long wigs and I have what can only be described as an adversarial relationship. They look great in theory, but they require a level of styling discipline that I sometimes struggle with.
One of my biggest early mistakes was not knowing when to stop messing with a wig. You start adjusting one strand, then another, and before you know it you’ve somehow made it worse than when you started and now you have a bird’s nest.
Because of that, I’ve quietly eliminated a few potential cosplay ideas over the years—even ones where I liked the character—simply because the wig situation would have been a nightmare…my failed attempt to cosplay as Hatsune Miku immediately comes to mind.
All of those experiences eventually shaped the kind of cosplays I prefer today.
These days I gravitate toward simple, comfortable costumes that I can wear for long convention days without constantly adjusting things. And no long wigs or characters with crazy hairstyles that take a master’s degree to style.
That’s one reason you’ll notice a lot of school uniforms in my cosplay lineup. They’re comfortable, practical, and surprisingly versatile. Swap a wig, change a ribbon or jacket, and suddenly you’re a completely different character.

These days I favor comfortable cosplay that can survive an entire convention day such as this Kyoko Mogami costume.
From a purely practical standpoint, the flexibility of school uniforms or say, a generic maid dress gives those costumes a pretty high return on investment, which is always appreciated when you’re dealing with a hobby that can get expensive fast.
Of course, one thing I had to get used to pretty quickly with crossplay was the attention it brings.
Since I don’t naturally have a particularly androgynous appearance even with makeup, which is still very much a work in progress even after all this time, I knew going in that I was probably going to get some looks or the occasional comment. Over time I got used to it, and at this point I can mostly shrug it off to the point where I don’t even know anything was said unless a friend mentions it.
What’s funny to me is that those moments are actually such a tiny fraction of the experience because the overwhelming majority of cosplay interactions are the exact opposite.
People who love the same characters and series you do.
The random hallway compliments, the excited “Hey, I love that character!” moments, the photos, and the conversations with fellow fans—that’s the part that sticks with you.
Fifteen years later I’m still learning, still improving, and still finding new characters I want to bring to life at conventions.
With a pretty stacked convention calendar this year—Fanime, AX, Dragon Con, Anime Los Angeles, and possibly Katsucon—it looks like year fifteen of this hobby is going to be a very busy one. Which means plenty of opportunities to keep refining things, trying new characters, and probably discovering a few more lessons the hard way.
Looking at my current cosplay lineup — both the costumes I already own and the ones still on the way — I’d say that crossplay experiment in 2011 turned out pretty well.
And honestly?
Stepping outside my comfort zone like that might be one of the best decisions I’ve ever made as a fan, even if my wallet says otherwise.





