Cross-dressing: my 10 tips for getting started

You are about to begin, or you have just started this journey towards the person you want to be.

Whether it is for fun, to experiment, or to affirm your gender, whether you are a travesti or transgender, you are about to experience an incredibly exciting and very intimidating moment at the same time.

There are so many things to consider… from choosing the right clothes to learning makeup, to expressing your feminine personality in a way that suits you.

Drawing on my experience with my clients, in this blog post, I share 10 tips for beginner travestis, and of course for transgender people, to help you look and feel your best.

My first tip is… radical!!

Lilly femme travesti en séance de maquillage chez Transbeauté

1. Invest in a good wig

I warned you!

What an amazing feeling the moment you wear your hair.
And what about the thrill you get the very instant your hair falls over your shoulders and when you lift your fringe?

All my clients will tell you, that moment is unique.

Investing in a good wig is an excellent first step for any beginner travesti.

A wig can instantly transform your appearance and also gives you the chance to try different hairstyles and looks.

Look for a high-quality wig in a color and style that flatters your face.

2. Learn basic makeup skills

If you’re just starting out, makeup can seem daunting. But hang in there because makeup is one of the most important tools to feminize your appearance.

Don’t worry about complicated makeup techniques (like false eyelashes or contouring) at first.

Instead, focus on lipstick and simple eye makeup, like eyeshadow and mascara.
They are easy to apply and will enhance your appearance even if your technique isn’t perfect.

Of course, there are many online tutorials that can guide you.
However, from the start, get professional help as soon as possible. (To read or re-read my article: Maquillage 4 raisons de choisir une pro)

Your self-confidence will be much stronger.

3. The hair removal hunt is open!

It is important to shave your face to look as feminine as possible.

Use a good razor and shave just before dressing to have a fresh, clean face with no signs of cuts.

Obviously, it would be ideal to shave or wax your body too. You will look more feminine, and female clothing feels softer on smooth, shaved skin.

We are not equal when it comes to body hair. We pull, we cut, we dissolve (guess what those depilatory creams do?).

You do what you want, but the hair must be as discreet as possible.

4. Create feminine curves

Feminine curves are undeniably attractive. That’s why most travestis will want to start their journey with breast prostheses.

Invest in a pair of breast prostheses that suit your body proportions. (Not too big and not too small.)
Silicone breast prostheses can cost hundreds of euros, but if you’re just starting, look for a cheap pair. There are plenty of offers online.

And don’t forget the detail that changes everything…

Hip and butt pads are the key to creating curves, even if it’s something you can invest in later.

5. Know your measurements

If you prefer to shop online, like many beginner travestis do, it’s crucial to know your measurements.

Men’s and women’s clothes have different sizing. Also, sizes vary by brand. If you know your measurements, you can check size charts before ordering clothes online.

This will save you many sizing mistakes.

To get your measurements, use a tailor’s measuring tape and measure the following areas:
• Bust (with and without breast prostheses)
• Chest
• Waist
• Hips

Here are some additional tips to make sure you take accurate body measurements:
• The measuring tape should be snug but not too tight.
• Make sure to keep the tape parallel to the floor.
• Take your measurements in front of a mirror to ensure the tape is level.

Even better, ask someone else to take your measurements for you…

6. Wear clothes that make you feel good

Now let’s move on to the fun part: shopping! One of the favorite moments.

When you start crossdressing, it’s about experimenting, so look for clothes you like.

Don’t buy anything boring just because you think you “should” wear it. Treat yourself! We all went through a "neon pink" phase; then it passes… and we sort it out!

Also, don’t spend too much on expensive clothes while you’re still figuring out your style. Again, there’s plenty of online options.

Feeling good is also linked to comfort, so don’t wear super tight corsets, 12 cm stilettos, or anything that looks like torture. (Unless, of course, you want to!)

Lilly Femme travesti en bottines dans un escalier

7. Choose the right shoes

Shoes are important for completing your look. High heels can instantly make you feel more feminine and attractive, even if you’re just staying at home.

Besides their obvious sex appeal, heels also affect your posture and give you a more feminine sway when you walk.

If you have a limited budget, invest in a pair of basic black or nude pumps that go with everything. Heels under 7 cm tend to be easier to wear if you’re just starting out. Ankle boots, especially in winter, are also a great compromise.

Finding women’s shoes in your size can be difficult. Lucky are those whose size does not exceed 41. But once again, the magic of the internet means you will find the perfect fit.

8. Go out with confidence (when you’re ready)

If you’re like most beginner travestis, your journey will start in the privacy of your own home.

That said, you may reach a point where you want to go out publicly. It’s an incredibly intense step and can be a great validation for your feminine self.

Plan ahead to make sure it’s a good experience.
If it’s your first outing, go to a place where people are used to seeing travestis and transgender women (like a friendly LGBTQ bar cf Lilly’s article où sortir à Paris en 2022. (2023 version coming soon)

You can also bring a friend or partner to support you.

Lilly sur le pas de porte en trench coat

9. Don’t worry about your “passing”

“Passing as a woman” is considered the Holy Grail for many travestis and transgender women, however, it’s simply not practical or easy for most people.

Instead, your goal should be to feel good in your skin. It’s normal to want to be close to perfect as a woman, but that doesn’t mean you have to look exactly like a cisgender woman.

I believe you should already be proud to be seen as an attractive and elegant travesti.