First Time Going Out Dressed? 10 Things Crossdressers Wish They'd Known Before

I'll never forget my first time going out dressed. I was terrified, excited, and absolutely convinced everyone was staring at me. Spoiler alert: they weren't. But I made just about every rookie mistake in the book, and I've heard similar stories from dozens of guests on My Girl Life Podcast.

So if you're thinking about taking that big step and venturing out into the world as your femme self for the first time, let me save you some of the anxiety (and blisters) I went through. Here are 10 things I wish someone had told me before my first outing, and trust me, your feet will thank you for number 7.

1. Choose Your Venue Wisely

Your first time out shouldn't be at the grocery store on a Saturday afternoon. Start with a crossdresser-friendly environment where you're expected and welcomed. LGBTQ+ bars, trans women and crossdressing meetups, or even a drag show night are perfect starting points.

I remember going to my first crossdresser social at a local LGBTQ+ community center. Walking through those doors was still nerve-wracking, but knowing I was in a safe space made all the difference. Nobody judged my slightly crooked wig or my amateur makeup job, they just welcomed me with open arms and plenty of helpful tips.

2. Invest in a Good Wig First

If you're going to splurge on one thing, make it a quality wig. A good wig can instantly transform your look and give you the confidence boost you need. Plus, it's way easier than growing out your hair or dealing with complicated styling.

I started with a cheap synthetic wig from Amazon, and let's just say the photos from that era are... well, they exist. When I finally invested in a human hair wig that actually looked natural and stayed in place, it was a game-changer. You can experiment with different styles, colors, and lengths without commitment.

3. Practice Your Makeup at Home (A Lot)

Do not, I repeat, DO NOT, try a complicated makeup look for the first time right before you head out the door. I learned this the hard way when I attempted contouring for the first time at 7 PM before an 8 PM outing. I looked like I'd been in a fight with a bronzer brush, and spoiler: the bronzer won.

Start simple. Master the basics: foundation, simple eyeshadow, eyeliner, and lipstick. You can build up to the fancy stuff later. Practice with drugstore makeup so you're not stressed about wasting expensive products while you're learning. YouTube is your best friend here, I probably watched hundreds of makeup tutorials before I felt comfortable.

4. Know Your Measurements Before You Shop

Men's and women's clothing sizes are completely different universes, and if you're shopping online for your first outfit, you need to know your actual measurements. I'm talking bust, waist, hips, inseam, all of it.

I once ordered what I thought was a "medium" dress based on my men's shirt size. When it arrived, I could barely get it over my shoulders. Measure twice, order once. Trust me, the disappointment of waiting for a package only to find out nothing fits is a real mood killer.

5. Forget About "Passing"

Here's the truth bomb that took me way too long to accept: you probably won't "pass" as a cisgender woman on your first outing, and that's completely okay. Obsessing over passing creates so much unnecessary anxiety and takes all the fun out of the experience.

Some of the most confident crossdressers and trans women I've interviewed on the podcast are the ones who stopped worrying about passing and started focusing on expressing themselves authentically. Rock your unique style. Own your look. The people who matter won't care, and the people who care don't matter.

6. Shave. Then Shave Again.

If you're showing skin, you need to be meticulous about shaving. I'm talking the closest shave of your life, done right before you get dressed. Use a fresh razor, good shaving cream, and take your time.

For your face especially, consider shaving twice, once with the grain, once against. I know it sounds excessive, but even the slightest stubble will show under makeup and in certain lighting. Some of my podcast guests swear by epilators or laser hair removal, but for your first time, a really good shave will do the trick.

7. Break In Your Shoes (Seriously)

Those cute heels you just bought? Do not wear them out for the first time on your big outing. I made this mistake and literally couldn't walk after two hours. My feet were covered in blisters, and I spent the rest of the night sitting at the bar wishing I'd worn flats.

Practice walking in your heels at home for at least a week before your outing. Walk around your house, practice going up and down stairs, get used to the height and balance. Start with lower heels (2-3 inches) and work your way up. And for the love of all that's holy, bring a pair of flats in your bag as backup.

8. Bring a Friend or Ally

Everything is easier, and way more fun, when you have support. If you have a friend, partner, or spouse who knows about your crossdressing, ask them to come along for your first outing.

My friend Sarah came with me to my first drag show, and having her there made such a difference. She helped me touch up my makeup, reassured me when I got nervous, and made the whole experience feel like an adventure instead of a test. Plus, it's just more fun to share these moments with someone.

9. Start Small and Build Up

You don't have to go from zero to full glam in one night. Maybe your first outing is just getting coffee at a quiet café. Then next time it's dinner at a restaurant. Then a bar. Then a club.

Building up gradually helps you get comfortable in different environments and situations. It also lets you figure out what you enjoy. I thought I'd love going to clubs dressed, but I actually prefer more low-key settings like wine bars or brunches with friends. You won't know what feels right until you try different things.

10. Have Realistic Expectations (But Still Have Fun)

Your first time out probably won't go perfectly, and that's okay. Your wig might shift. Your makeup might smudge. You might feel self-conscious. But you're also going to feel incredibly alive and free in a way you've probably never experienced before.

The goal isn't perfection, it's taking that brave first step toward living more authentically. Every crossdresser and trans woman who's now confident in public had a first time out, and most of those first times were messy and imperfect and absolutely beautiful anyway.

I've talked to so many guests on the podcast who say their first public outing was a turning point, not because everything went smoothly, but because they proved to themselves they could do it. That's what matters.

You've Got This

Look, I get it. The idea of going out dressed for the first time is terrifying. But it's also one of the most exhilarating experiences you'll ever have. Every confident crossdresser you see out there started exactly where you are right now, nervous, uncertain, and wondering if they could really do this.

Take these tips, do your preparation, choose a supportive environment, and then just go for it. The crossdressing community is waiting to welcome you with open arms, swapped makeup tips, and probably some really good stories about their own first times out.

And hey, when you do finally take that step? Come find me at a meetup or drop me a message. I'd love to hear how it goes. We're all in this together. 💕