Crossdressing Tips

Crossdressing Tips

Crossdressing can be simple and complex at the same time. You can go as far or as minimal as you want. Crossdressing can mean wearing a pair of panties underneath your clothes or going as far as shaving your whole body and getting hundreds of dollars’ worth of makeover. It is entirely up to you.

It will, however, take time and practice as well as lots of mistakes from first-timers and might even end up costing a lot of money. It is simply about discovering yourself and trying to find out what you like, how you like it and what you are comfortable to wear.

It’s about finally uncovering a part of yourself that you might not get out very much. It usually takes a lot of time and patience to get where you want to be. It may be quite tough for first-timers and even on those who have been doing it for a while. You might not look and feel as well as you had imagined, but that shouldn’t put you down. Eventually, you will get there as it is something you learn by doing.

To help you in this journey, we have put together this guide with crossdressing tips.

What Is Crossdressing?

Crossdressing can be defined as the act of wearing clothes and other accessories that are associated with the opposite sex. It can be used for the purpose of disguising oneself or for comfort and a form of self-expression that has been used throughout history.

Each society has a set of norms, guidelines and even laws that define what type of clothing is most appropriate for each gender. Thus, gendered clothing is largely a social construct. There are many people who feel uncomfortable with adhering to this construct, and this is where crossdressing comes in.

It must be remembered, though, that crossdressing is simply an action and does not indicate any specific cause for such a behavior. There are many people who incorrectly correlate the action with a homosexual or transgender, but the term “crossdressing” is not synonymous with anyone’s gender identity or sexual orientation.

Crossdresser Clothes

crossdresser clothes

Just like gendered clothing, crossdressing is also socially constructed. For example, in Western societies, pants or trousers have been worn for a long time by women, so it is no longer regarded as a form of crossdressing. Thus, a woman dressing in “men’s” clothing cannot be said to be crossdressing anymore.

Similarly, there are cultures where men wear skirt-like garments such as a sarong or kilt. Thus, they are not seen as clothing for women alone and have been accepted throughout history. With modernization and societies becoming more globalized, men’s and women’s clothing are adopting dressing styles of other cultures. Hence, traditional men’s and women’s clothing styles are changing to introduce styles that would otherwise be associated with the other gender.

Even so, a man dressing in clothes normally designed for women is still frowned upon in most societies. This is why the act of crossdressing is now largely associated with a man dressing in traditionally feminine clothes.

Shopping for crossdresser clothes can be hard and easy at the same time. In order to find the clothes that best fit you, you have to try them on. You would probably not know which size you are with women’s clothing, so in order to figure that out, you must try out a few sizes to find the right fit.

For example, you might wear a medium-sized T-shirt in men’s clothing, but in women’s clothing, you might have to get yourself an extra-large size mainly because you may have broad shoulders. Moreover, a small waist size can mean you can wear a size 8 skirt, but if you have broad shoulders, that means you would have to get a size 12 for a dress.

Thus, there might not be one size that will suit you and it may vary. It is a good idea to measure yourself before you venture out shopping for your clothes. You should measure yourself from the following parts:

  • You should measure your waist at the belly button
  • Measure your bust at nipple height without any padding or foam
  • Measure your bust at the nipple height with padding or foam
  • The chest should also be measured under the pectoral muscle, which is around 2 or 3 inches below the nipple

When it comes to shoe sizes for women, these are generally one and a half size larger than the male shoe size.

MTF Makeup

crossdressingt tips

Crossdressing makeup can be hard and will cost you money, time and lots of practice. You must realize that you cannot achieve the look you want on the first or even the fiftieth time you try. You have to keep at it in order to get what you want.

There is a lot you can do to get you to your desired look. You can watch videos online and learn how people are doing their makeup.

Similar to buying clothes, you need to consider what you like. Everyone is different, so what works for one person may not work for everyone else. Hence, you will need to find your own techniques eventually.

Everyone has to use makeup according to their skin color, tone and skin, which you will eventually learn by practice. Similar to clothing, all cosmetic companies have different shades and products, which you will eventually learn about. You can always schedule a makeover with somebody you are comfortable with to get you started on the learning process.

Be prepared, however, as makeup is generally expensive and you will get what you pay for. You can always start with cheaper brands when you are just experimenting and move on to the higher quality ones as you learn. After all, it is better to practice how to put on eyeliner with one that costs $8 rather than a $30 eyeliner!

The basic tools that you will require are:

  • Makeup sponge
  • Cotton pads
  • Cosmetic cotton buds
  • Sponge tip applicator
  • Middle-sized brush for blush
  • Wide brush for powder
  • Small brush for lipstick
  • Eyeliner
  • Lipstick
  • Finishing powder
  • Mascara
  • Concealer or corrector
  • Eyeshadow palette
  • Blush
  • Highlighter
  • Eye pencil


Most of the times, when people think about shaving their legs or other parts of their body, they wonder what other people will think. You must realize that you should not care what they think about. Every time you change something about yourself, there is a chance that somebody will say something negative about you. That will happen in any case. Hence, try not to think about them.

There are plenty of ways to remove hair, so you should find one that suits you the best. Crossdressers generally shave their legs, arms, chest, their back and wherever else they feel comfortable. The whole point is to get smooth and hairless legs and body to feel wonderful.

The first time you would be shaving, be prepared for some nicks and cuts. This may make you frustrated, but with proper practice and time, you will learn.

You can use an electric clipper in order to remove as much hair as possible. This is what you can do prior to shaving if you have never shaved your legs before. It will help make the process easier if you have a hairy body.

The best time to shave your body is when you are in the shower as it will open your pores and provide a better shave. Also, while you are in the shower, you can easily relax, sit and learn about the curves on your body and how to use the razor on them. Shaving your body is quite different from shaving your facial hair, so you need to know your body.

Patience is very important here. The first time you shave, you will realize it takes forever. However, with practice, the duration will eventually decrease.

When it comes to facial hair, most people prefer to get their eyebrows threaded as it gives a nice, clean look. If you also want to go for this, know that the ideal time is to get it done every three weeks. It may hurt a little, but it is quite affordable and convenient.

Remember that after you shave, apply a moisturizer to keep your skin soft.

Tips on Crossdressing

Set Your Goal as a Crossdresser

If you have decided to try crossdressing, the best way to go about it is to have a plan. It will help you get where you want to be twice as fast and for a lot less money. It is good to do some homework first so that you do not end up investing in things you will never end up wearing. Take your time to write down your plans and get a feel of the feminine impression you desire to recreate. Trust us, you would be glad you did not jump into wasteful purchases.

Most people get a sense of their feminine side by wearing lingerie. It represents quite a distinct form of femininity. Most people feel a sense of how it is like to be a woman the minute the silk touches their skin. Many even start out by “borrowing” pantyhose from their mom, sister or even girlfriend or spouse. If your goal is personal pleasure, you should invest in basic inventory to enhance that feeling.

You can get the basic makeup and clothing to achieve that goal. Painting your nails can also be a great idea while you explore this feminine side of yours with silky lingerie and bright red fingertips. There is no need to be an expert. Sometimes, you just need to go with the flow.

sexy crossdress outfit

Have an Online Existence

If you find pleasure in private crossdressing, you can look at the web for images of other crossdressing men, transvestite clothing and MTF makeup techniques. You can even develop an online existence and join the discussion. The internet can not only help you get more tips on how to do a lot of things but also allow you to meet other crossdressers, share your opinions and make likeminded friends globally.

Get Rid of the Shame

There are many things a lot of us have done in private that we feel ashamed about. As we grow up, we realize there is nothing to be shameful about if it is a part of your personality. For instance, most young boys have felt guilty for masturbating while growing up, but eventually, everyone realizes it is a part of life and a part of finding yourself and your unique personality.

In the same way, crossdressing is nothing to be shameful about if you feel a connection with it and love how it feels. In fact, something that feels so good cannot be so wrong, right? There are many more people just like you, from the White House to Wall Street. You should not feel alone or guilty for just being yourself.

Crossdressing is a normal behavior. When you are ready, you can even move from being a private crossdresser to a more public one.

Preparing the Skin for Applying Makeup


If you have not shaved, even the best makeup would look terrible. Make sure you do not have any unnecessary facial hair.

In case your skin gets irritated after a shave, use some softening aftershave products. Even applying ice cold water to the face will help close the pores on the skin.

Cleansing the Skin

Before you start applying any makeup, you must make sure your skin is thoroughly clean of oil and dirt. Simply apply a cleanser or toner, wait for about 15 minutes and wash it off. We recommend a toner with a tightening effect, but of course, your choice will ultimately depend on your skin type.

Preparing the Skin

After you are done with cleansing the face, you should apply a primer or moisturizer on your face. The consistency and type of moisturizer depends on your skin type. Special primers can also be used to hide any evident wrinkles or pores.

Fixing Imperfections

If the primer or moisturizer is not enough, you may use special correctors or concealers to hide any blemishes on your face. The color of these products should be according to your skin tone. Do not be afraid if they end up looking like spots on your face; they will eventually disappear as you apply the foundation.

Taking Care of Your Hands

Along with clothes and facial makeup, the other important factor to consider is taking care of your hands. Generally, your hands say a lot about you. An average man’s hand is larger than a woman’s, so it is important to take care of it and make it look feminine. You must start with going for a manicure or doing it at home by yourself. You may clip your nails, push back the cuticles and clean underneath the fingernails with a brush. Always apply a moisturizing cream to keep them soft. All this should be made a part of your regular routine if you want to see optimal results.

Taking Care of Your Feet

Just as you need to take care of your hands, you must take care of your feet. Imagine how it would look if you are wearing gorgeous shoes with cracked heels or ragged toenails! You must treat yourself to a pedicure at least twice every month where you exfoliate your feet, clean and clip your toenails and moisturize your feet.


Exfoliation is the process of getting rid of dead skin cells from your skin. It will end up giving you soft and smooth skin, which looks younger and more feminine. Make sure you exfoliate your face and body once or twice a week using a washcloth, loofah and an exfoliating scrub. For the face, only use facial products. Never use a body scrub on your face as you could end up facing disastrous consequences.

Face Mask

Apart from a proper cleansing ritual for your face, using a face mask every week should be a part of your beauty regimen. You can target a particular skin care concern or simply use a relaxing mask to pamper yourself. You can use specific masks for acne-related issues, wrinkles or even for basic radiance and softness.


There are plenty of crossdressing tips out there which you can benefit from. The above is not an exhaustive list, and it can be added upon. It is just the basics on how to get started with crossdressing when it comes to how to clothes and MTF makeup techniques. There are many other ways of looking more feminine like taking care of your skin and overall body. The best way to go about it is to be comfortable in your skin and find out what works for you. As we have mentioned already, everyone is different and what works for one person may not work for all.

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