Lessons I Learned Dressing in Drag for Halloween

Dressing up in drag for Halloween wasn’t just about putting on a costume — it was a journey into a world I never expected. Here’s what I discovered in my three ventures into drag:

1. A Different Kind of Interaction

Women interacted with me in ways that were refreshingly open and relaxed. Conversations flowed freely, touching on topics that usually never surfaced. Apparently, complaining about killer heels makes for a great icebreaker. Maybe women feel safer with a less traditionally masculine presence around, or perhaps it’s just that drag blurs lines and breaks barriers.

I found myself fielding curious questions about my “boobs” (filled with bird seed), inquiries about what I did with my anatomy (didn’t tuck), and even discussions on bathroom logistics (sitting down was the only option, really). It turns out, women who’ve dressed as men for Halloween report similar experiences — clothes truly do shape how we’re perceived.

2. The Glamour of Getting Ready

Dressing up was an eye-opener into the Herculean efforts women undertake. As a guy, getting dressed typically involves a few straightforward steps. But for women, it’s a symphony of moisturizers, primers, foundations, and a bewildering array of makeup choices. Eyeliner alone felt like a Sisyphean task — I couldn’t even keep my eyelids steady, let alone open.

Then there’s the undergarments — boxer shorts versus pantyhose is a universe apart. Shapewear might sculpt you into a goddess, but don’t expect to eat or breathe comfortably. Bras? Let’s just say they redefine the term “uncomfortable.” After spending over two hours transforming, I gained a newfound respect for anyone who makes this routine.

3. Embracing Compliments

Normally, compliments make me squirm with discomfort. But in drag, every “you look beautiful” and “great legs” fueled a rush of endorphins. It made me realize how powerful and uplifting a genuine compliment can be. Now, I make it a point to spread that positivity — it brightens someone’s day and lifts my spirits too.

4. Stepping Outside myComfort Zone

When my wife suggested a French Maid costume, my initial reaction was panic. As a balding accountant/lawyer combo, this was definitely uncharted territory. But embracing the challenge led to an adventure — shopping for heels at Payless, finding wigs at Party Boy, and navigating a boutique specializing in risqué Halloween attire. It was liberating to dive into the absurdity of it all.

Fully committing to the role meant mastering the art of high heels and DIY breast forms. By the time the parties rolled around, I was strutting confidently — even dancing in those heels (major kudos to heel-wearing warriors everywhere).

5. Reveling in the Unconventional

Each party brought more confidence and flamboyance. I relished the shock on friends’ faces when they realized the French Maid or Latex Nun was me. It was a surreal blend of vanity and empowerment, interrupted only by the occasional awkward encounter (note to self: creepy dudes, not cool).

6. Lessons in Empathy

Above all, this experience heightened my empathy. Feeling uncomfortable in a bar line from a creepy dude’s advances gave me a tiny window into what women endure far too often. It’s eye-opening how a change in attire can change interactions.

In Conclusion

Dressing in drag wasn’t just about costumes and makeup — it was a crash course in empathy, confidence, and embracing the unexpected. It taught me that our quirks and differences are what make us interesting. So, next time you’re hesitant about trying something new, remember: ordinary is overrated, and fun often lurks outside our comfort zones.

A Note of Appreciation

To my LGBTQIA+, BIPOC, misfit, and outcast friends: you’ve faced challenges I can’t fathom. Dressing up was a brief venture for me, but for you, being true to yourself is a lifelong journey. I stand with you, admire you, and am grateful for the light you bring to this world.

Let’s keep celebrating our uniqueness. Hugs and thanks for sharing your journey with me.

Join the Conversation

What’s your take on stepping outside your comfort zone? Have you ever tried something unconventional that turned out to be unexpectedly fun? Share your thoughts and stories below! Your feedback keeps the conversation going.