CD 101: Tips for Novice Crossdressers

| May 25, 2015
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Our role model.

Our role model.

So, you are a male who is very attracted to the idea of dressing as a woman. Their clothes, shoes, and hairstyles play a siren’s song at you as you go through your daily routine. “Wear me” they seem to say. Why we get these feelings is a mystery. Research into why men want to crossdress isn’t high on the list of things the human race wants to figure out so we just do what we do. We can take comfort that the urge to emulate women has been around for centuries. It wouldn’t be surprising to learn that Oog the caveman was caught by his mate wearing her spare leopard skin loincloth.

The important thing about crossdressing is to achieve a balance in your life that gives you time and the freedom to crossdress when you need to while letting you take care of the things you must handle in male mode. Give yourself permission to be who you are. If that’s a heterosexual crossdresser who needs to “dress up” on a regular schedule then go on and do it. If you don’t you will be miserable. Suppressing your feminine urges are likely to make you an unpleasant person.

Crossdressing and transsexuality are points on a trans spectrum and it’s important to identify where you are on that spectrum. Some who label themselves crossdressers are amazed to find out that they need to express their feminine component all the time. Some who identify as transsexuals are not good candidates for reassignment surgery. It’s important to sort these things out with a competent therapist who understands gender issues. The following guide is aimed at those who are satisfied with part time dressing as the opposite sex, but there are tips that are applicable to all of those crossing the male to female gender border for the first time.

A Short Guide to Crossdressing

If you are new to unleashing the inner lady you are no doubt wondering how to get started. It can be quite daunting. The majority of women spend their childhood and teen years learning the feminine arts. Starting from scratch as an adult male is quite a task.

Every male is different. Some will have masculine qualities that are difficult to hide. Some will have advantages such as shortness, less body hair or a light beard. Each crossdresser needs to find the things they need to change, temporarily in most cases — or permanently, if they are able, that will make their face and body conform more to that of The Basic Woman.

Basic woman on right. Makeup applied on the left.

Basic woman on right. Makeup applied on the left.

The Basic Woman

Every woman, without any makeup, jewelry or sexy, stylish clothing is the basic woman. She has soft skin; long hair or short hair cut in a feminine style; she moves and talks in a feminine way and her body has some curves. As a crossdresser, before you put on makeup and clothing, you must prepare your canvas. An artist has to get their canvas ready before any paint is applied and you are an artist whose canvas is your own body. The first step is to get your body and face ready by making them appear as close to the basic woman’s as you can.

Be Smooth

The majority of women don’t have beards or heavy body hair. They often have a fuzz on their faces and some have light, fine hair on their arms and legs. Some women have heavier hair on their legs. As a crossdresser attempting to look like a woman that hair needs to be removed. (Cultural rule!) For most part time crossdressers shaving is the answer. Your face needs to be as smooth as you can get it. There are plenty of shaving tutorials on the Internet and some here on TGForum. Every man’s beard is different and you need to experiment with techniques to determine which is the best one to give you the closest possible shave.



Leg hair can be shaved and should stay smooth for at least a day of femme fun. If you don’t mind a bit of pain, waxing will remove it for at least a week in most cases. Again, everyone’s leg hair is different and the removal method that works best and fits your lifestyle is the one you want to use.

If you absolutely can’t get rid of your leg hair due to concerns over family and friends noticing that you’ve banished it, you can disguise it. Get a pair of flesh-tone dance tights. (Available in stores that cater to dancers.) These are thick enough that the hair will not be seen. Then if you like you can add another layer of cover with regular nude, tan or black pantyhose. This method is effective but hard to wear in hot, humid weather. (Ironically, hot humid weather is when family and friends get together for outdoor activities and a closeted CD needs to be able to show their hairy legs.)

What about electrolysis or laser hair removal? Both are effective ways to get your beard or body hair removed but both are expensive and take time. If you are only dressing up once or twice a week is it worth the money? And after you have developed your beard the skin around the hairs is not smooth as a baby’s bottom. Even after a beard is removed you can have a different skin texture in that area. Also, if you are active in your male role you will look strange as a man. With no beard shadow (and shaped eyebrows) you won’t look “normal.” No beard shadow makes a male face look older, as if all the beard hairs have gone gray. So before permanently removing anything evaluate the necessity. Is it worth it to you to look odd as a male in order to look better as a female?

Arm Hair Tip: If you have hairy forearms you can try trimming it down every few days with an electric razor’s sideburn trimmer. Lightly go over the hair and take off a little every few days. Friends and colleagues will in most cases (there can be someone who is super perceptive) not notice that the arm that was formerly hairy is now smooth. A tan helps disguise the bare skin, too.

Femme Eyebrows

Male brows. note the many hairs around the main brow.

Male brows. note the many hairs around the main brow.

We are in a time when more shaped and sculpted eyebrows on men are considered acceptable. If you are a white collar worker you are more likely to not attract attention if your brows are trimmed, plucked or waxed. Blue collar men typically don’t pluck their brows. So what to do if your male lifestyle won’t let you make your brows look more ladylike?

There are techniques that work to tame your bushy male brows. One method calls for using a glue stick and face powder. You coat the brows with the glue stick, press them down and then powder them with a flesh-tone powder. This is a method used by drag performers. After two to three applications the brows are pasted down and almost invisible. They are covered with foundation and powdered again. Then the performer draws on flamboyant brows with an eyebrow pencil. This is most suited to the stage or going out to a nightclub. In daylight the pasted down brows will be more noticeable.

Your brow goal.

Your brow goal.

A variation on the glue stick method is more subtle and better for daytime. You pluck extraneous hairs around your brow area so the main brow has a defined border. Take spirit gum, the adhesive used by actors to apply false beards, and coat the brow hairs with it. Let it dry a bit. Then you press the hairs down and shape them into a more feminine style. (A cuticle pusher is a good tool to use for this. Or a thin dowel rod cut at an angle.) Let them dry and then fill in with an eyebrow pencil. Your formerly bushy male brows are now crossdressed.

Cover Up That Beard Shadow

If you have a dark beard it’s important to cover its shadow completely. After your smooth shave you need to apply moisturizer. Let this set for at least 10-15 minutes. Then you’re ready to apply a commercial product called Beard Cover. This is sold in theatrical supply stores. You can order it online from the Alcone company. It’s made by Ben Nye theatrical makeup and it comes in three shades. Each shade is the color opposite to the color of a different shade of beard shadow. Most dark beards make a blue shadow. Beard Cover FS-1 is the opposite of that shade and when applied over the beard area is neutralizes the blue. Science! (Some people recommend using red lipstick instead of the commercially available Beard Cover. If this works for you, fine, but lipstick is formulated for lip wear.)

Note Jon Hamm's beard shadow.

Note Jon Hamm’s beard shadow.

Beard Cover is applied as thinly as possible using either your fingers or a makeup sponge. After you’ve covered the beard area set the beard cover with powder. Press the powder into your skin with a puff. Brush off the excess powder with a makeup brush. If you have problem areas where the beard shadow shows through you can add a concealer to that area. (Upper lip can be one of these spots.) MAC cosmetics makes a good concealer or you can use Dermablend. Cover your whole face with a foundation that matches your skin tone. Face, forehead and neck all need to be the same tone and it should match the color of your chest. Now your face canvas is ready to apply eye makeup, lipstick and highlights. YouTube is filled with videos on how to do all that, including several by our own Chanelle Nirok.

Shape That Body

As mentioned previously, the basic woman normally has some curves. Generally speaking women have larger hips, smaller waists and rib cages, and their shoulders/upper bodies are not larger than their hips. (Not always though. I saw a woman in the supermarket today who had shoulders larger than her hips.) Since males can’t do much to diminish their upper body most will have to do some padding on the hips and butt while cinching in the waistline with an appropriate undergarment. (Lucky CDs will have hips that are close to the width of their shoulders.)

Example of a body shaper that provides compression for the waist and enhance the butt.

Example of a body shaper that provides compression for the waist and enhance the butt.

Corsets are not a good idea for day wear. They are too thick and are noticeable under any top that is slightly tight. The best undergarments for waist slimming are the Spanx® type. They are thin but the elastic is strong and will pull you in a few inches. Experiment with different styles and sizes until you find the ones that work for you. Clearance racks of body shapers at stores like Ross and TJ Maxx are a good source of cheaper priced shapers.

Waist cincher

Waist cincher

Now and then it’s possible to find waist cinchers that just go around your waist and pull it in. They close in the front with many small hooks. If you have a belly fat issue these will not reduce that, only your waist.

Hip pads and breast forms are available from online stores like The Breast Form Store. If you need to add a couple of inches to your hips and butt to balance out your shoulders they will have the sizes of padding that you need. Make sure you experiment with your breast size by stuffing your bra with things like socks. Once you’ve established what size breast looks good on your body you can go ahead and spend money for silicone breast forms.


"Evette" available from The Breastform Store.

“Evette” available from The Breastform Store.

The crowning glory of your feminine image is your hair. If you have long hair then you are able to wear your own and that is the best, most natural look. If you don’t have long hair it’s time for a wig. Many novice crossdressers will go to a Halloween Adventure store and get a cheap costume wig. You’re not doing yourself any favors buying a cheap wig. You can find quality wigs online at The Breast Form Store and other Internet shops that will serve you better in the long run. Watch for sales and don’t spend hundreds of dollars for human hair wigs. They don’t last any longer than synthetic wigs and there is more upkeep involved.

Everyone has a hairstyle that flatters their face. Finding that style is easier today than ever before since you can take advantage of apps that will put various hairstyles on a photo of you. (Apple has a free one for iPhone and iPad, There is an Android app, too.) Put on your makeup, pull your own hair back if needed, and take a good photo of your face. The photo is uploaded and the app will allow you to virtually try on many hairstyles. When you find the one that’s right for your face go with it. A good hairstyle will help disguise male features and highlight your feminine look.

Shoe Notes

Whose shoes?

Practice before going public in these.

Many of us are attracted to wearing extreme stiletto heels and they do look great. But, if you can’t walk in them with poise and grace they can completely undermine your feminine image. Many women can’t walk in them and there’s nothing as big a turn off as some well dressed woman hobbling along in shoes she is afraid she is going to fall out of at any minute. When you’re starting to go out in public to show off your new look go out in stylish flats and work your way up to the higher heels. You may want to stick with flats if you’re over 5’ 10” since three or four inches of heel will put you well above six feet. That, however, depends on whether your intent is to blend in or be noticed by one and all. In any event, before wearing extreme heels in public practice, practice, practice. The biggest reason women can’t walk in their extreme heels is that they only wear them when they go out. Wear them around your house all evening. You will enjoy that and you’ll be getting the practice you need to pull them off well when you’re out and about.

These are just a few of the things a novice crossdresser needs to work on for their best possible feminine image. Staying in shape, watching diet and doing regular skin care are also things you need to pay attention to. The bottom line is, you have this urge to dress up like a woman. Do the best job you can and get out there and enjoy your femme self. If you have ideas for more crossdressing tips you’d like to see here let me know.

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Category: Impersonation, Transgender How To, Transgender Opinion


About the Author ()

Angela Gardner is a founding member of The Renaissance Transgender Assoc., Inc., former editor of its newsletter and magazine, Transgender Community News. She was the Diva of Dish for TGF in the late 1990s and Editor of LadyLike magazine until its untimely demise. She has appeared in film and television shows portraying TG characters, as well as representing Renaissance on numerous talk shows.

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  1. Me’Schell Me’Schell says:

    I think this was very well done. It was easy to read and to understand. It was done with the utmost professionalism. From the novice and the beginner, I still enjoy reading things pertaining to us. It’s people like you that have brought us this far and will continue to help us grow. I deeply want to thank you, it’s people like you that makes this world a better place for us to know that we belong. I enjoyed it.
    With The most sincerity, You are truly loved.
    “Thank You” Micheal
    AKA Mee’ Schell. XOXO