How to Start Crossdressing: 8 Beginner Tips for Confidence and Style

How to start crossdressing can be a prickly subject. You may want to do it, but something’s just holding you back. For many, nervousness and uncertainty take the top spots on why they can’t start their crossdressing.

For others, it can be overwhelming. But here’s the thing: it doesn’t have to be! Taking one step at a time isn’t illegal!

For those new to crossdressing: start small and work your way up. No need to rush into an entirely new wardrobe. Instead, choose one or two items that make you feel comfortable and confident. Confidence grows over time, and so will your style.

There are more simple tricks for smoother crossdressing. If you’re curious what these tricks are, hang about! I’ll walk you through a few simple steps to make crossdressing easy, fun, and stress-free.

1. Start Small with Comfortable Basics

When I first started crossdressing, I thought I had to go all out right away. Big mistake! Starting small is underrated, but it works the best.

I began working with the simple items, like stockings and panties. Honestly? Using simple things made the whole experience a lot less intimidating. A pair of stockings under my jeans? No big deal, but there’s a definite change I can literally feel. The thrill of it helped me get used to the feeling.

The idea is to ease into it. New things will definitely feel foreign, so you have to familiarize yourself with the new sensations. You can start by wearing panties or bras under your regular clothes, for example.

It’s also a great way to keep things low-key if you’re not ready to go all out in public. This helps build your confidence without feeling too exposed right away.

2. Find Your Unique Style

No crossdresser knows what their style was immediately. Most just knew they wanted to feel good in what they wore. Figuring that out may take a little trial and error— and that’s totally okay.

I found that experimenting with different outfits and accessories helped me discover what made me feel the most confident and comfortable. Some days I felt amazing in a cute, frilly dress, and other times, I preferred something a bit more casual.

Crossdressing is all about personal expression. So don’t be afraid to try new things until you find your style.

I’d recommend starting with different fabrics and cuts. Sometimes you’ll be surprised at what you like. For example, I didn’t think I’d love silk until I tried it. Now I wear it all the time!

Thrift stores are also a goldmine for this. These places are great for experimenting without spending too much.

If you’re unsure what aesthetic you most identify with, Roanyer’s Thanksgiving Day Sale from November 18 to 24 is the perfect time to experiment with variety. With orders over $899, you’ll receive a Free Crossdressing Kit, included wig, headpiece, maid dress, stockings, and underwear.

3. Practice Makes Perfect (Especially with Heels)

Maybe you’re thinking, “Pshh, heels. How hard can it be?” If you do, you clearly haven’t tried to walk in a pair! It’s actually trickier than it looks. So when you finally train to walk in heels, remember to have unli patience!

Also, if you’re just starting out, don’t grab the highest stilettos you can find. Go with something lower and more manageable, like a small block heel or a cute kitten heel.

Many make the mistake of trying a tall pair of heels first and nearly end up with a twisted ankle. The key here is to work your heels up. At first, it may feel like walking on stilts. But with time and practice, you’ll find your balance. Soon, you’ll strut confidently in higher heels without feeling like toppling over.

Other (Not Heels) Considerations

The same goes for your overall presentation. Whether it’s the way you walk, your posture, or even the little gestures, it all takes time to feel natural.

You can also practice how you move, stand, or control the “gender knob” (voice feminization). Don’t rush yourself— confidence comes with practice. When you do things at your own pace, you’ll feel much more comfortable and self-assured.

Remember, no one gets it perfect right away. (Except maybe SpaceX with their rockets and “Chopsticks.”) So, take your time, and don’t be too hard on yourself. Each time you practice, you’ll notice small improvements. Those add up to big boosts in your confidence.

4. Invest in Quality Breast Forms and Shapewear

Sure, women come in many figures. But creating an obvious feminine silhouette will make your confidence soar to high heavens. Plus, it’ll make your clothes look so much better.

Breast Forms

The first secret to the feminine form? Breast forms.

Breast forms, especially silicone ones, are perfect for adding those womanly curves. They fit naturally under any clothing. They also give your chest a more realistic feminine appearance.

Shapewear

Shapewear is another secret to nailing that female silhouette. It smooths out your figure, helps with your posture, and just makes your clothes fit better overall.

Shapewear is a lifesafer especially if you’re fond of wearing tight outfits. It hugs your body in all the right places and helps accentuate your natural (or padded) curves.

5. Start Learning Makeup Basics

For newbies, makeup can feel like a whole new world. With just the number of makeup products available, it sure does feel overwhelming. But once you get the hang of it, you’ll be surprised to realize that it’s one of the processes most crossdressers enjoy.

Makeup can transform how you look in just a few brushstrokes. But it can also transform how you feel. It promotes confidence in a way that’s hard to describe until you try it for yourself.

Dealing with Makeup

Like other Crossdresser Tips 101, do with the simplest makeup routine first. Full glam sounds nice, but you won’t use it everyday anyway.

So focus on the basics: foundation, mascara, and lipstick. Foundation evens out your skin tone. Mascara gives you deer-eyes to make you look more feminine. Lipstick ties the whole look together. When you’re ready, learn contouring and subtle eye makeup too. These will help you soften your face, making it more feminine.

Makeup Guides

There are tons of guides out there that can walk you through everything step by step. Don’t feel like you have to figure it out on your own!

With makeup, practicing is necessary. Don’t worry if your first few attempts aren’t perfect. There may be a few “clown face” moments, but that’s part of the fun! Over time, you’ll find the techniques and styles that work best for you. Just keep experimenting until you get it right!

6. Plan Your Public Appearances Carefully

The first time I went out in public dressed as a woman, I was so nervous I could barely breathe! I’m not going to lie. It was scary. But you know what got me through it? Planning ahead.

When the time comes and you want to bless others with your crossdressing self, you should consider the “Where” with seriousness. Start with low-key places. Those where you won’t feel too much pressure.

My choice then was a quiet movie theater. There, I could easily blend in without worrying about attracting much attention. Cafes or libraries are also good options since they’re usually calm. In these places, often, no one’s paying any mind to what others are wearing.

When you’re planning your outfit, think about where you’re going. Is it casual or a bit more dressed up? You should always dress for the occasion if you don’t want eyes on you. Imagine if you wear a cocktail dress to a coffee shop! You won’t just look a bit out of place. You’ll look ridiculous!

Gradually build your confidence by selecting environments where you feel comfortable. Then, move on to busier or more public places like shopping malls or restaurants.

To best sell your feminine appearance, get Roanyer’s Silicone Bodysuit or Hip-Enhancing Pants.

7. Build a Supportive Wardrobe

As a crossdresser, you can’t just do away with wearing the same thing again and again. But, you also don’t have to buy an entire department store! The keyword here, then, is curating a “versatile” wardrobe.

With a wardrobe like this, you’ll mix and match crossdressing outfits with less hassle and stress. A versatile wardrobe often includes:

● Little black dress

● A couple of casual pairs of jeans

● A few skirts

These staples will give you endless options for any occasion— whether hanging out at home or planning to go out.

Accessories come in next once you have the basics:

● Wigs

● Belts

● Jewelry

All of these are the finishing touches that really pull a look together.

You can, but there’s no need to go overboard with completing your crossdressing wardrobe. Begin with a few key pieces, then build from there.

With this in mind, Roanyer’s Black Friday sale is the perfect opportunity to expand your wardrobe! It offers up to 75% off on crossdressing kits, wigs, and accessories. It’s an amazing chance to grab everything you need to round out your look without spending too much.

8. Shop Smart During Black Friday

If there’s one thing I’ve learned, it’s that crossdressing can get expensive. You essentially give birth to your new persona, so it’s not surprising to give that new persona its separate crossdressing needs.

That’s why I always look forward to Black Friday, and Roanyer’s sale is one you won’t want to miss. Roanyer online store has unbeatable discounts, free gifts, and curated bundles that are perfect for newbie crossdressers.

To make the most of this sale, you need a game plan! Shop early because the best items tend to sell out quickly. It’ll bum you out if you miss out on one of the best sales this year!

Roanyer also offers daily flash sales throughout November on its most popular products. So you better keep an eye on those you want to grab if you want to save even more. One more thing— if you’re ordering from Roanyer’s overseas warehouses, you can get free shipping. Such a nice bonus, huh?

Conclusion

Crossdressing is all about expressing yourself and feeling good in your own skin. If you’re just starting, remember to take it slow— start with small, comfortable items, practice your makeup, and build your wardrobe one step at a time. Investing in quality products like breast forms and shapewear is essential for achieving that realistic, feminine look and feeling your most confident.

And don’t forget— Roanyer’s Black Friday Sale 2024 is your chance to stock up on high-quality crossdressing essentials at up to 75% off. With daily flash sales, giveaways, and huge discounts, it’s the perfect opportunity to snag everything you need to look and feel amazing!