The First Ten Items Every Beginner Crossdresser Should Buy

Cross-dressing requires not only technique but also supplies and materials. It’s a complex art with many different layers. As such, beginners tend to be overwhelmed by the amount of stuff they have to buy. There are so many items that they don’t even know where to start. Sometimes, it causes them to lose interest and give up on cross-dressing. Some even get depressed.

But you can start making a list based on your priorities. To some people, certain items are more important than others. In this article, I’ll discuss the ten most essential things for beginner cross-dressers. I’ll also elaborate on what makes them valuable to us, so you can decide which ones are more suitable for you. If you’re in doubt, you should read this article!

1- A basic set of makeup

I know, this sounds obvious since we’re talking about cross-dressing. Makeup is essential to disguise and conceal our masculine facial features. It helps us make our complexion more feminine, which might be the most critical aspect of our transformations. But feminization techniques are a bit more complex than conventional makeup and require a lot of different products. As such, some beginner cross-dressers don’t know what to buy and get confused as they’re unfamiliar with that stuff.

Because of that, the first item I recommend for them is a basic makeup kit consisting of a few essential items. I would include a foundation that matches their skin tones. After that, a shade palette for contouring, including lighter tones for highlighting. Plus, some eyeliner, eyeshadow, and mascara. These are the bulk of what every cross-dresser needs. And as a finishing touch, lipstick and eyeshadow would be nice. You can also include a makeup case for easy storage and some tools to apply it for a practical effect. However, you don’t need all that extra stuff as a beginner. I’m mentioning them for convenience, but you should consider them if your budget is large enough. Just as about everything on this list, it will depend on many circumstances, such as the space you have and your patience to start dressing up. As such, you can either buy it all at once or gradually build up a stash.

2- Shapewear based on your body type

Besides our facial features, body shape differs from the male and female stereotypes. Cross-dressers are well aware of that and use shapewear to reduce these differences. For our sisters, the general guideline is to make their bodies look curvier, similar to an hourglass. We achieve that by adding or removing mass from some regions of our bodies. And techniques involve either relocation of body fat through compression or adding mass with paddings.

The particular kind for you, however, depends on your body type. To summarize things, I can say that thinner cross-dressers would make better use of padding. Use them to add volume to your chest and hips, creating an hourglass effect compared to your waist. However, a corset might do the trick if you’re a bit chubby. It compresses your waist, relocating its mass to your chest with a similar hourglass effect.  

On the other hand, the average body might benefit from a combination of both techniques. Take your time to analyze the options, but include them in your shopping list! After all, shapewear makes all the difference in how we perceive our bodies. For more info on that, check out this other article:

https://www.roanyer.com/blog/padding-vs-compression-what-kind-of-shapewear-is-ideal-for-you/

3- A high-quality wig

Ah, yes, hairstyle! Studies show that this is one of our defining features and makes a lot of difference in how others see us. It is also something tied to gender stereotypes and one of the first criteria for the gender perception of others. I know that nowadays, it’s common for us to see short-haired women and long-haired men. And it doesn’t necessarily affect the way we perceive their gender. That’s because it has more to do with the hairstyle than the length. The problem is that not every cross-dresser can let their hair grow long or even get a feminine haircut. And this is what makes wigs so crucial to us.

For both cross-dressers and drag queens, and sometimes for trans women, a wig symbolizes femininity. They are a practical way of getting a feminine-looking hairstyle without us spending a lot in a hairdresser saloon. Besides that, they allow us to try different hairstyles and colors in minutes. These advantages more than make it up for the costs and downsides, including the care we must take with them. As such, I consider a wig an investment. Choose a hairstyle that you like, and grab the best quality wig in your favorite style you can find or afford. It makes a lot of difference in the final results, and it’s way better than buying several cheap ones. I speak from experience; You won’t regret it.

4- A miniskirt

Miniskirts are something many of us desire deep inside. These are considered one of the most feminine garments and make us feel like attractive girls. This is the first “shock” some of us have about the differences between feminine and masculine wear. Starting with that is a way of creating confidence and encouraging other experiences. It’s a rupture that helps you deal with fragile masculinity and have some personal growth as a person.

But besides that, it also encourages us to take further steps in our cross-dressing adventures. Using a skirt and experiencing these feminine sensations pushed me towards shaving my legs and tucking for the first time. This is only an example of what it can do for our journeys. Cross-dressers are innovative and bold by nature. And the best way to experience this aspect of ourselves is by pushing our limits and setting new boundaries. As such, exploring new territory while a beginner will make you feel unstoppable! So go on, buy a miniskirt and try out some bold outfits afterward. You deserve that joy!

5- A black dress

Can you think of anything more feminine than a dress? I would be surprised if you said yes. These have been associated with femininity for ages! To be honest, dresses are not my favorite outfit; they don’t match my favorite style. But even so, I still have a couple! A few dresses are essential for any cross-dresser’s wardrobe, as they add some variance and new outfit possibilities. But since dresses have been around for so long, there are many different types. They come in a variety of shapes, colors, and sizes! But with so many options to choose from, where should we start?

My recommendation for first-timers is a plain black dress. It’s not as girly as a pink cottagecore dress, but it’s more versatile. You can use it on any occasion and match it with any kind of accessories. Besides that, it brings some feminization advantages as well. Black dresses help highlight your curves, outlining your silhouette. It’s a nice effect, especially for beginners, since it boosts their confidence and self-esteem. As for the length, I recommend reaching down no further than your knees. That’s because this way, you get the same encouragement as with the miniskirt!

6- Underwear

Another common thing among cross-dressers is their curiosity about wearing panties. Male underwear is designed to accommodate our masculine features. But the designs are dull, and the material is not exactly comfortable. As such, we long for the same underwear as girls since it matches our cross-dressing tendencies. The feminine designs help us deal with gender identity issues, and the whole experience is thrilling for beginners. It’s so good that some of us use the even while in boy mode.

Other advantages of wearing female underwear include the possibility of discreet cross-dressing. It’s a relief for those who haven’t come out yet. Besides, it encourages you to practice tucking techniques to perfection and perhaps to shave more often. I see it as an opportunity for you to explore an intimate side of cross-dressing and maybe take a few sensual pics to increase your confidence. You certainly don’t want to miss out on that, so I recommend you buy at least a few. I say that because multiple panties allow you to wear them more often, as we do with boxers. Nonetheless, it is, without a doubt, a mandatory item for beginners and pros alike!

7- Something to put inside your bra

It is time for me to address the most apparent thing men lack compared to girls. I’m talking about a nice pair of breasts! It is one thing that lots of cross-dressers worry about, and it tends to be a massive blow to their self-esteem. After all, how can we look feminine without boobs? Many of us spend years perfecting techniques to create a perfect cleavage, but we must start somewhere. As such, “How to make fake boobs” is one of the most searched topics on the internet by young cross-dressers. But what is the best approach for first-timers in that scenario?

Well, there’s no shortage of methods, I tell you that. But the most suitable ones for your situation will depend on how dedicated you are or how much you can spend. The most basic technique is stuffing your bra with whatever you can find. But if not done correctly, the results are laughable. It requires effort to work, including a proper underwired bra to hold everything in place. If that’s your plan, include one on your list. As for the stuffing, avoid the classic newspaper balls or socks. They break the illusion and won’t move as the real thing. Instead, go for balloons filled with water or grains. They have a better weight and will look more natural.

Another technique involves pushup adhesives and some makeup. However, it works better with chubby cross-dressers. The idea is to use the pushups to relocate your chest mass, simulating boobs. Use an underwired bra to give it a better shape and makeup to create an illusion of depth. It works wonders for visual purposes, creating a realistic-looking cleavage. Still, movement is not a thing with this method. As such, you can combine it with the previous one for an even better result!

Now, I want to talk about my favorite method. This one is becoming more accessible thanks to companies such as Roanyer. And I hope that, soon, every single one of our sisters will be able to afford one. I’m talking about breast forms! They come in many shapes and sizes, some simple and others complex. The classical approach is individual silicone forms. These can be either adhesive or inserted inside a special bra. While cheap, those are limited and sometimes fail to create a decent-looking cleavage. The modern method includes silicone vest-like breastplates or even full bodysuits. They are pretty convincing and create a seamless effect. So much so that they allow you to wear revealing outfits. You can even wear lingerie or a bikini without giving away that you’re a cross-dresser! Another reason I recommend them is the silicone gel filling. It makes them move and bounce like the real deal. It’s hard to notice the difference! It’s an investment but, without a doubt, a “Must-buy” item for beginners.

Take your time to think about your situation and which of these techniques is more suitable for you. Ultimately, what matters is that you get something to fill your bras and add volume to your chest. You’ll be one step closer to becoming the girl of your dreams as soon as you do that.

8- A choker necklace

I must also mention that one thing in your neck. It’s one of the quickest ways to tell a cross-dresser apart from a cisgender woman! If you plan to go out en femme without getting clocked, you should pay attention to your throat. Do so to hide the bump we know as Adam’s apple. Some people who practice voice feminization might be able to hide it naturally. They do so without covering their necks. But it’s a technique that takes time to master, and first-timers won’t be familiar with it. They tend to find it quite complicated. As such, multiple failed attempts might discourage them from proceeding with cross-dressing.

The usual approach is to hide the neck area completely. Scarves are a well-known method used by cross-dressers and trans women alike. It’s so popular that it has been used since the 1920s. They’re still fashionable enough, but some problems have become evident. The most concerning ones are regarding comfort since scarves are hot. They were created for heating purposes, after all. It makes them unsuitable for certain climates or weather. Apart from losing popularity in the past decade, that is.

One thing going in the opposite direction, though, is choker necklaces. Goth culture made them famous first. But they were so well-received that many other styles incorporated them. They are much smaller, more portable than scarves, and more comfortable. You can wear them in a way that covers your adam’s apple without restricting your movement. And I’ve also heard that wearing them during voice training makes things easier! I’m trying it myself to see if I get any results.

9- A self-care kit

Self-care should be part of every cross-dresser’s routine. Not only is it good for our self-esteem, but it also makes us look more feminine. Soft skin and a delicate complexion are powerful feminization tools. We can achieve that through self-care. The opposite, on the other hand, is negatively associated with masculinity. Cross-dressers should take care of themselves from the very beginning of their journeys. The longer they do it, the better the effects.

You can start with a selection of moisturizing creams after every shower. These will smoothen your skin and make the shaving process far easier. You may also add exfoliating creams and sleep beauty masks. These will make you look younger and more beautiful while en femme. The last thing in the kit is a sharp razor and shaving cream. Use them to keep your face, arms, and legs well-shaven and with feminine aspects!

10- Cardboard boxes!

Okay, they don’t have to be made of cardboard. But you will need more than a few boxes for storage purposes. If you’re still a closeted cross-dresser, they should be discreet. That’s why I suggested cardboard to begin with. But if you feel like you don’t have to hide that stuff, you can get creative.

Make sure you can store everything you buy without damaging it. Some of that stuff, like wigs and shapewear, will require some space. But you may fold clothing articles in general, and makeup doesn’t occupy much space. To keep everything intact, ensure it’s a moisture-free location with decent ventilation. You can ensure that by poking small holes in the boxes! But the point here is that investing in storage and maintenance is as essential as investing in your feminine wardrobe. After all, you don’t want to lose your cross-dressing stuff due to poor storage.

Summary

This list contains essential items for the average cross-dresser. It’s a nice place to start, but feel free to adapt it to your needs. Here, I included detailed descriptions of what makes these items important. You can use it as a guideline for your purchases or as a reference to decide what’s more suitable for your reality. Each of us experiences cross-dressing differently, with different goals. So it’s okay to disagree. My goal is to help all of you as much as possible, so I hope you enjoyed it. As such, if you have any other suggestions or information to add, please leave a comment! Tell us what you think about this list and how helpful it was, according to your goals.