Thinking about Makeup

For some this aspect of crossdressing is a real burden.

I like to present the best feminine image I can when I dress so I only tend to do so when I have the time to do the makeup properly.  I’ve found that if I only have a short window of opportunity to dress, spending an hour on my makeup routine reduces the time I get to spend in the clothes I love, so I end up rushing it.  That invariably means I’m not happy with the final result and I don’t enjoy the dressing experience as much as normal.

So I tend not to dress unless I have the whole day to pamper myself.  That way I actually enjoy the makeup routine – you could even say that it enhances the whole experience and helps me to get into the female frame-of-mind.

If you’re just starting out on your crossdressing journey, or if you’re thinking of adding makeup to your dressing experience, it can be rather daunting.  If you’re anything like me the idea of sitting down at the makeup counter in your local store probably fills you with dread.

I was lucky enough to get some great coaching in the application of make-up from the girls at Transformation during my many makeover sessions there.  But if you can’t afford to visit such establishment you can learn the basics without “outing” yourself!


Wash Your Face

Always start with this one.

I know it may seem obvious but it’s often overlooked – it’s always better to begin with a clean face.

The main tip here is to try and be gentle. Don’t scrub your fac. Use a good cleanser and rinse well to remove it all.

After washing it’s a good idea to apply a toner to refresh your skin.


Use a good quality razor and shave as close as possible, being careful to avoid nicking your skin.

Shave first in the direction of hair growth, then lather-up again and shave in the opposite direction. That way you can pretty much guaranterr that you get the closest shave possible.

It is best to shave immediately following a hot shower so that the pores are open. If you don’t plan on showering first (or you don’t have time), wrap a hot towel around your face for the best results. Rinse your face with cool water after shaving to close the pores back up.

You should wait at least 5 to 10 minutes after shaving to apply makeup – the skin needs time to recover from the razor.

If you have time you might consider trying a clay mask in addition to cleansing and shaving. Clay masks draw out impurities in your skin and provide a smoother surface for applying makeup. A smooth surface is the most important aspect of good looking and easy to apply makeup.


You’d better get used to this word because you’re going to see it a few times during  this post!

Dry skin tends to soak up foundation, which ends up spoiling the effects of applying makeup. Make sure to use an oil-free variety.

Moisturising provides a good base for your foundation. Be sure to wait until the moisturiser is soaked into your skin before moving on to applying foundation.  If you want to feel extra-femme you could try a moisturiser with a nice, feminine smell.

Apply Foundation

If you are using a liquid foundation, apply it using your hands to spread it on your face, just make sure you smooth it out with a sponge without pulling or stretching your skin. Be extra careful and gentle around the eyes where the skin is very thin.

Set your foundation with a loose powder. On hot days, foundation will require periodic touch-ups.

Concealer should go on after the foundation.  You may need a heavier foundation if your facial hair tends to grow quickly.

Eye makeup

Eye Shadow

Apply some translucent or foundation powder to the eyelids and brush off excess. This will help the eye shadow go on easier.

Start off by applying a light shadow to the entire area from eye to eyebrow. From the outer corner of the eye to the outer edge of the eyebrow, apply a darker shade of eye shadow and bring in 1/3rd directly above the eye.

Eye Liner

When you’re doing this it would help immensely if you have a magnifying mirror.  You can get some fairly cheap double-sided mirrors (with one side normal and one side magnified).  It can help with the application of all makeup, but it’s especially useful when applying  eyeliner.

Use liquid with fine line brush and start at the inner upper edge of the eye. Slowly bring the tip over the lash line and out to the outer edge of the eye. This may overlap the base of your false eyelashes.

Use a water-base liner as it is easier to correct any mistakes and easier to remove at the end of the evening.

Use liquid liner or pencil on the lower lash. Try highlighting only the outer third of the lower lash to make the eye appear larger. Do not make this area too dark for daytime use.


If false eyelashes are used, mascara is not necessary for upper lashes, but can still be used to blend lighter lashes with the false lashes; also can be used to show off the lower lashes.


Your lips need 3 things.

Firstly, keep them moisturised. Invest in a chapstick and use it, even if you’re not crossdressing. The cracked skin on dry lips will catch on your lipstick and peel off chunks of colour, making your lips look rough and splotchy.

Ssecond, lip liner. This looks like a lot like eyeliner (and generally it actually is the same stuff, just in different colours).  It’s a heavier makeup than your lipstick.   Lip liners do a couple of things: 1. they help define your lips and 2. they prevent your lipstick from smearing.

“Normally” you would pick a lip liner to matches your lipstick colour, but you can get some nice effects by pairing a lighter colour such as pink with a red lipstick or a darker colour like maroon with red lipstick. Experimentation is the key here – you can find your own favourites – have fun with it.

Concealing Those Masculine Features

Learning how to use makeup to hide masculine features is one of the essential keys to “passing” as a woman. The wonders of modern makeup offer any number of ways to help hide the aspects of a man’s face that make him look most masculine.

Invest in a heavy-duty foundation and beard cover. The beard and moustache areas are hard to cover with normal makeup, but there are several great “concealer” products out there designed to provide maximum coverage. Be warned that these aren’t cheap.

Take the time to source a very good powder that matches your concealer/foundation. For top-notch results, you want your face to look as natural as possible. Hiding masculine features is key, but you also want to blend the makeup so that it doesn’t look like you are hiding anything. Having a top-end concealer and a matching powder is the first best tool in your makeup arsenal.

Use eye makeup to obtain maximum femininity, but try to use it sparingly. The eyes are arguably the most beautiful part of the face, so you should enhance them with a nice shade that accentuates your own eye colour.  Go for a top-end mascara that does not clump – again use just enough. If the eyes look too heavily made up, they look fake and and ‘amateurish’.

Pluck your eyebrows.  You won’t see many women with thick eyebrows. To achieve maximum femininity, you want to shape and groom them by tweezing or waxing.   See my previous post on the subject.

Select the perfect lipstick and lip liner. This varies depending on skin tone, hair and eye colour. If you are a brunette, you might try something in the plum line. If you are blond, you should consider pinker tones. The main point is to keep the lips subtle while still drawing attention to their beauty

Makeup Removal

Leaving on makeup longer than necessary will lead to clogged pores, especially if it is thick makeup or there you have trowelled it on.

Removing the makeup as soon as you can after you’re done is key to keeping attractive skin. However, it can be tricky to make sure all of it is gone.

Remove eye makeup.

Use a gentle makeup remover for eye makeup.

Regular makeup remover can irritate the eyes. This is one area that you’ll need to check closely to be sure you get most, if not all, of it off.

Steam your pores.

Drape a towel over your head and hold it over a sink of hot, steaming water. This opens your pores and dislodges your makeup, making things easier for cleansing.

Remove your lip colour.

Apply a small dab of petrolatum jelly to your lips, and gently rub it in with a tissue. Fold in the tissue, and blot the lips.

Use a gentle face wash.

Most of your makeup ought to come off on this stage. Be sure the face wash is gentle and you don’t scrub harshly. Your skin has been covered in makeup all day and it needs to breathe!

Remove any eye makeup that ran while you washed your face. It is common to see a small bit of mascara or eyeliner under your eyes, and simple to remove with a dampened cotton swab.

Close your pores with a splash of icy water.

Pat your face dry with a towel and rub in a light moisturiser.

Finally, if you’re still apprehensive, please check out my post “An Alternative to YouTube?“. There you’ll find a link to a page with some very good “how to” videos on the application of makeup.

Don’t worry about getting it wrong – you’re only human after all – just enjoy the learning experience.

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