10 Tips for Beginner to Start Your Crossdressing Journey

As time goes by, society as a whole tends to become more open-minded. As it happens, crossdressers, trans folk, and LGBT people, in general, are starting to feel safe. With such an increase in acceptance, more of us are coming out of the closet, inspiring more and more crossdressers to start their own journey. It’s really sweet to see our numbers increasing, as our community grows stronger, but we must remember that newcomers may need our help to proceed. Most of them aren’t well prepared for that, and a bit of assistance can make a difference.

In order to start your crossdressing adventures on a good note, you must pay attention to small details and plan your purchases. Try to understand what is your body type, and what are your goals as a crossdresser, so you don’t lose your focus. Practicing is key in order to improve your skills, and tracking your progress may enhance your confidence. When shopping for clothes, be careful, and avoid buying things you won’t use. Also, don’t be too concerned about passing as a woman, since it’s not the main point in crossdressing.

I don’t want to see our sisters giving up on their dreams, so I wrote this article with helpful tips for beginner crossdressers. In order to make sure they persist, my objective is to clarify common questions and provide some guidelines for them. It includes makeup techniques, suggestions of outfits and general information that they may find to be useful. As self-esteem plays a major role in a crossdresser’s life, I’ve also included a few paragraphs on that subject.

1. Getting started with makeup

Makeup holds a very important position among all other things in crossdressing. It’s the core of your transformation. Believe me when I say it: your body, even if it has curves, won’t make you feel feminine when your face still looks masculine. And once you manage to feminize your face, you’ll be halfway through the crossdressing process. That’s how important it is, so I guess it’s a good way to start this article.

Well, my very first tip on this topic is to always buy quality products. When buying your first makeup supply, give preference for reliable and trustworthy items. I know they are usually more expensive, but that’s worth it. I say that because there are a lot of cheap, fake cosmetics around there. Not only can they harm your skin and give you an allergy, they are also unreliable and easy to come off. If you start your crossdressing by making use of them and get bad first results, the chances of giving up increase.

Now, I need to teach you how to apply your makeup the right way. What you want to do is to conceal your masculine features, while emulating feminine ones. It may include your jawline, eyebrows and nose, with further applications on your cheeks, eyes, chin and forehead. The general idea is to use darker tones to “push away” some areas, and lighter tones to highlight others, such as seen in the image below. If you wish, you can use this same technique to create “natural” cleavage.

Needless to say, shaving is very recommended. It’s almost impossible to hide a beard or mustache with makeup (Hats off to Cesar Romero for trying it back in the 60’s). Use a good shaving gel to ensure you remove as much facial hair as possible and wash the razor between strokes so it stays sharp. After you shave, you may possibly notice that the shaved area is still slightly darker than the rest of your skin. That’s because the remains of your facial hair are still there, creating a dark bluish area called “5 o’clock shadow”. Sometimes, it’s even noticeable through the makeup. To get rid of it, you may have to do a color correction. It consists in applying a red tone in the area (usually lipstick or red eyeshadow) before the makeup foundation.

2. Shapewear and curves

Making your face look feminine sure is important, but you may feel incomplete without a feminine-looking body. Trying to achieve feminine curves may seem challenging, but it’s not impossible. Actually, it’s probably way easier than you may think. To do so, we must understand how different bodies work. Almost every single one of us wants an hourglass figure, but that’s not how it works. People have a vast diversity of body types, and we can’t fit them in stereotypes and beauty standards. Even so, we know some noticeable differences between most male and female bodies.

To reduce said differences, it’s recommended to use various types of shapewear. The most common is the good old corset, and it’s justifiable. One of the main differences between the bodies of men and women is how they allocate mass. Due to estrogen, females accumulate fat on their hips, while men do so on their waist, creating a visible difference between both shapes. A corset compresses the user’s waist and reallocates body fat. Thus, men can use it to make their bodies look more feminine, granting them some curves.

To enhance such an effect, hip pads are recommended. They will make your hips and butt look bigger, and your waist even thinner. Of course, I recommend getting some Roanyer silicone pads, which you can fit inside your hosiery. But some other options include padded panties and DIY foam pads. These options will make your legs curvier than ever, but you can also make them smooth and sexy. To do so, you’ll need a few pantyhose options. A thick black one is useful for almost every occasion, but if you want a more “revealing” outfit, you can adapt it. The trick is to use two different hoses at once. A thick one, in a color similar to your skin tone, and a sheer black one on top. It will look like some of your skin is still visible through the black hose, and your legs are smooth and hairless.

My final advice concerning shapewear is about a thing lots of crossdressers struggle with breasts. It’s not a secret that they are one of the things most people first notice in a woman, and it’s no different with crossdressers. It’s not a mandatory item on our list, but it does help with self-esteem and feeling feminine. The method you should use varies according to your goals, which may change for different situations, so I’ll discuss a few. As I’ve mentioned earlier, makeup can be used to create cleavage, but it won’t give you volume or movement, so it’s better fitted for pictures. Volume and movement can be created in a number of ways, such as with a silicone breast form or a stuffed bra.

Each “stuffing” has its own advantage, but folded socks are most recommended. They won’t move too convincingly but are reliable and tend to stay steady in place. For a more realistic approach, you may try silicone breast forms. They let you create a very convincing cleavage despite being more expensive. My tip is to try as many methods as possible for each situation until you find out which suits your needs better.

3. Choosing appropriate clothing

How do you want to dress up? With clothes that can make you as feminine as possible, am I right? Well, it’s somewhat simple, but you still have to decide between multiple options. My goal in this section is to give you some directions and point out which clothes are better for you. It depends on your body type, preferences and availability of each outfit, so feel free to be creative. What I’ll say here is but a guideline, so don’t worry about being restricted by it.

Now, as I said, it may vary a bit depending on your body type. What do I mean by that, you ask? Well, your shape is very important to consider when buying your feminine clothes. That’s because you can use your new outfits to counterbalance your shape, feminizing your figure even further. If your shape looks like a triangle, give preferences to clothes that add volume to your upper or lower body, respectively. If you look more like a square or rectangle, add volume in both regions, and add spirals if your shape is rounder. Something you can do to get the grip on that is to look at your full body in a mirror. Picture the idealized hourglass figure, and compare it to yours. As you do that, you’ll soon be able to figure out where you need to add volume with clothing.

When selecting outfits, pay attention to the fabric and color as well. Thicker fabrics are useful to hide shapewear in a seamless way, while darker colors are going to thin your figure and outline your curves. You can also use color theory to balance your figure and look more feminine. To do so, use light colors to “reduce” and darker ones to “enlarge” parts of your body, aiming for an hourglass once again.

Last, but not least, buy only a few items at a time. If you overload yourself with new outfits, you won’t experience each one of them enough. You will soon feel like you’re wasting too much money with crossdressing. If you buy only what you need, you’ll be able to crossdress with more efficiency and enjoy your female side better.

No matter what you choose, if you are afraid to shop for stuff, you can always buy what you need online. This way, your outfits are delivered to your home, with as much privacy as possible! I recommend stores such as Amazon, Shein, and eBay. However, I must add that delivery time may vary from each store and that you should always check their return policy. That’s because you can’t try stuff before you buy them online.

4. Getting measurements

To choose the right shapewear, underwear, and outfits in general, you’ll need to know exactly which size you need. However, male and female outfits tend to use different charts, and different sizes altogether. Luckily, some crossdressers and trans people came up with conversion charts we can use to determine our female size for clothes.

First, take measurements of your waist, hips and chest. Convert them to female sizing, and you’ll get the three first measurements you need. You’ll use them to determine the size of your shapewear, stuffed bras, and underwear/legs without paddings. If you plan on using hip pads, consider that when measuring, and add roughly 5cm/2 into what you get. Better yet, take the measurements while wearing the pads.

After you get a corset and a stuffed bra (or breast forms), take new measurements, so you can apply them to the outfits themselves. Just make sure you keep both your measurements, with and without shapewear. This way you’ll be prepared for different scenarios, and able to use different outfits.

5. Passability

I know passing is a dream for lots of crossdressers. Even though it’s not the main goal for most, it’s awesome to be perceived and treated as a girl. It increases our confidence and makes our interactions with other people much easier. Even if it’s not your priority, don’t worry about that. Passing or not, every crossdresser is valid, but if you want to find out if you pass nonetheless, I have a few tips as well.

Do your makeup, put on your favorite outfit and go to the larger mirror you can find. Look at yourself and analyze your shape, then take some selfies and mirror pictures. You can show them to friends you trust, so they can give you feedback about your passability. If you want a more impartial opinion, try r/transpassing on Reddit or other crossdressing threads. If you choose to do so, make sure you don’t share NSFW or compromising pictures of yourself, as you can’t control their spread on the internet.

6. About comfort

Being comfortable is more important than it seems. If you feel uncomfortable when you crossdress, you’re unable to enjoy the experience, and your day as a girl is ruined. Crossdressing is meant to bring you fun and joy, so if you’re being hurt, something is wrong. The most common cause of discomfort is restrictive shapewear with high compression. If you feel you can’t breathe properly, it’s better to stop for a while and get shapewear of a bigger size.

Heat also plays a role in discomfort. Crossdressers tend to use more layers of clothing. With that in mind, try to keep your crossdressing environment well ventilated. If you own an AC unit, don’t hesitate to turn it on, especially if you want to do a complete makeover. Take a good shower before you start and drink a lot of water during the process. It prevents you from getting exhausted while you dress up, so you can enjoy the experience and feel like the girl you want to be.

7. Choosing a wig

A wig is also essential for the average crossdresser. Very few of us can grow natural long hair, and even fewer are happy with a masculine haircut. A good wig can totally change one’s appearance and make them look quite feminine. My tip is to choose one that suits your face and is in the same color as your natural hair if possible. I see wigs as an investment because low-quality ones (such as those from Halloween costumes) can ruin your look. If possible, buy at least two wigs with different hairstyles so you can vary your appearance.

Lace wigs are an extra step to look convincing, but they are more expensive. Cheaper alternatives are also valid, such as wigs with bangs or bonnets to hide possible flaws. It depends a bit on your budget but remembers that better quality wigs are more likely to help you pass if that’s your goal. What I want to point out is that the quality does matter and has a great impact on the results. With that in mind, think about how you imagine yourself as a girl, in different hairstyles, so you can choose a few good wigs based on that.

8. Practical tips on storage

Now, one thing that usually concerns both newcomers and experienced crossdressers, is storage. The bigger our collection of feminine stuff grows, the harder it is to store or hide it. Many beginner crossdressers want to keep it a secret. If that’s your case, start with only a few outfits, a wig, and basic makeup. Cardboard boxes and backpacks were my favorite places to hide my stuff when I started, as I could keep them on the back of my closet. If you have your own car, you can put your stuff in its trunk and keep it locked. My feminine shoes were kept with my regular ones, but right on the back of them, where no one could see it. Underwear is a bit more complicated, as it needs to be frequently cleaned for hygienic reasons. I washed it with my masculine ones and used to let it dry in my closet.

For the wig, make sure to have a few hair nets around it when you store it. They may hold everything in place and prevent possible entanglement. My tip is to place a hairnet around the front area of the wig, covering the top and the bangs. After that, gently fold the wig and place everything inside another net. Some wigs come with a paper ball inside to help them keep their shape. It’s quite helpful for storage and I strongly recommend keeping it. After that, place your folded wig covered by hairnets inside a box or a Ziplock bag.

9. Should I shave?

This is a recurring set of questions among crossdressers all over the world. Is shaving really necessary? What are the benefits of it? How do I start shaving without being discovered as a crossdresser? And the list goes on. Well, let me tell you how I see this issue, in order to clarify most of these questions and give you a few tips later on.

First of all, I want to point out that shaving is far from being mandatory. You see, women have body hair too, it’s a natural thing, and it includes hair on the legs, arms and armpits. Facial hair, on the other hand, is quite uncommon, so I’d say that shaving is important for crossdressers that want to look feminine. Even so, I must add that I am very aware of the social pressure that exists upon female bodies. This way, those with less body hair are usually considered to be more attractive. Body dysmorphic disorder is another issue that sometimes can be related to this subject.

Despite us knowing that it’s normal for women to have body hair, our dysphoria makes us want to shave. That’s so we can be seen as “more attractive” to the beauty standards. In this kind of situation, shaving can help us to deal with it and is even recommended. The biggest benefit of shaving is that it makes us more comfortable with our own bodies with little effort.

Even though some of us are afraid of shaving, it doesn’t really make it obvious that you’re a crossdresser. It won’t give you away, like makeup and other things would do, since you can say it’s a matter of hygiene and discomfort. It’s normal to be uncomfortable with body hair, as sometimes it can be itchy and such. That’s what I said the first time some relatives questioned me about my shaved legs and arms, and they bought it. If you really don’t want people to find it out though, you can use pants more often to hide it. After all, there are even some alternatives to shaving. One of such is combining long-sleeved shirts with multiple layers of pantyhose.

10. A word about body language and voice training

Every crossdresser should know that being feminine can’t be summarized into the way you look, but newcomers do not always know it. There are much more details than just that, and every single one of them plays a major role in making you look feminine. This section is more important to beginners that want to pass as a woman, but everyone can benefit from it.

Well, the first detail that needs to be addressed is body language. It doesn’t matter how feminine you look, if you move like a man you will be clocked and won’t be able to pass. A good example is posture, as men tend to have a straight “T” posture, with weight balanced between both legs. A more feminine posture consists in doing the opposite. Instead of being centered, the weight in women’s bodies tends to be kept at one side, in a posture that resembles an “S”.

When sitting, males will spread out and occupy a lot of space. Women, on the other hand, usually try to avoid that and sit as “closed” as possible. Take this advice when standing up as well and try to look tall instead of wide. It works well to make you look more feminine most of the time. Also, keep your gestures in mind all the time. Being feminine means being more expressive than your male self, but don’t exaggerate. Try slow movements, keeping your shoulders back and elbows tucked. About facial expressions, smile more, do NOT avoid eye contact, and you should be fine.

Your feminine voice is one of the most difficult things to master in terms of crossdressing. My advice for beginners is to avoid talking at first until you build confidence, but never give up on practicing it. I do have a few tips on it as well. You should avoid getting to a “falsetto” voice by bringing your pitch too high. You must find balance and pulling your Adam’s apple up is a good start. Try recording your voice, and listening to yourself, or ask a friend you trust for some feedback on how you sound. A good option that might help you, and which I have been using recently, is the Voice Pitch Analyzer app on the google play store. It’s completely free and analyzes how your voice sounds. It also gives some text samples for you to read and see for how long you can keep your female voice.

So these were my main tips for crossdressers that are starting their own journeys. They are broad and general, in order to apply to as many people as possible. Make sure to keep practicing, and never give up on your dreams. Crossdressing is an awesome activity, and each crossdresser experiences it in their own way. All of them are valid, as long as you’re having fun and being true to yourself. Before you go, please leave your comments and share your thoughts if possible, as your opinion is very important!