Application of Makeup in Order to Make a Masculine Face More Feminine
This "tutorial" will focus mainly on the face, touching generally on use of clothing for a "total" appearance. I will try to cover things important for part-time and full-times as well.
PLEASE KEEP IN MIND - where referring to the differences in appearance, this is obviously not going to be truth for all men. Just like the concept of beauty, the difference between male and female has no exact formula that will work for everyone's face.
ALSO : This is not focused towards Drag Queens or outrageous female makeup - this may be a starting point, but Drag is more a fantasy and though there are some general concepts - something you just need to be creative with, not limited to a set of ideas about.
1. Hair. Current culture dictates, women generally have longer hair than men. Cut of hair is extremely important - the cut needs not only to be "feminine" but to flatter your face. You can have your hair (or wig) cut to minimise a prominent jawline - from what I've seen, curly or wavy hair or hair with layers angling inwards works best. Short hair can work, too, but it's more exacting and if you're really trying to pass, you may want to start with long first unless you have a very feminine face or a very skilled and accepting stylist.
Long hair in a single-layer blunt cut is not very feminine. Shorter, "flippy" hair is feminine, but takes a good deal of work.
Women's hair tends to be lighter than men's - women bleach their hair as it is a biological sign of female fertility in Caucasians especially.
1, A. To apply a wig. Women's foreheads tend to be shorter, so there is really no need to apply a bald-cap. Hair should be slicked back if it is short, and covered, though (to protect the wig - the less you have to wash it, the longer it will last).
NOTE : Obviously, you do not need to follow all ideals to a T, and doing so is not that important - you must simply effectively tip the balance in what the average person sees when they look at you. No one thinks Catherine Zeta-Jones is a man because she has dark hair - it's a complex combination of things that produces an overall effect.
Also, it might be best to get a "perfect" wig or custom wig rather than cut it yourself if you don't have experience cutting hair. A wig that is cheap enough for you to risk cutting it without skill is cheap enough it will look fake and ruin the overall effect you're going for. Using your natural hair is best, but I understand not everyone wants to have it styled to appear feminine all the time.
Oddly, I have found that spiking the hair is feminising - perhaps because of the volume. It is important in female hairstyles that there be "volume" around the face - it makes a HUGE difference than having a limp hairstyle.
2, A. Facial Hair. Obviously, none. Women have "peach fuzz" but this cannot be imitated well. Your best bet is in waxing all facial hair (lasts longer, shaving grows back in hours).
B. Eyebrows. Female eyebrows are more arched and thinner. Also, they should be slightly lighter than your hair colour for best effect (you may bleach - some reputable salons will do this, or you can do it at home if you're very careful, I did it once and to a friend, I'm not blind and neither is she).
If you want to do this temporarily, your best bet is probably in a latex cover for the eyebrow - you can try to "block them out" but it is not always effective for thicker brows.
You can then draw on a new pair (as natural, using tiny delicate strokes to simulate hair, or as theatrically Greta Garbo as you want).
To shape your natural eyebrows, try using foundation to cover up the parts you want to remove to get an idea of how the shape effects your face. The shape should follow the curve of your eyes and 90% of the time, you want to remove from the bottom, not the top (though you may have to to create an arch). You will most likely want to pluck some of them away from the center - generally to about where the sides of your nose are, sometimes less with a very wide nose. Close eyebrows are masculine.
C. Eyelashes. An eyelash curler is actually not a waste of money and makes a big difference. For a subtle look, use brown mascara - or brown false eyelashes. If you have a dark complexion, black will look natural (but not on lighter ones).
Applying false eyelashes is easy. You just dab the latex glue on the part that goes on your face, making sure to get a little extra on the ends and let it dry for about a minute - then apply carefully (I think it's best to apply from the end closest to the nose if you're using a full set - this saves you from accidentally applying that too far away - which looks really weird.
D+E. Moustaches + Beards. A general note for areas with facial hair - if you've only shaved, not waxed, you will have a cool-colour / bluish / greying tone to the skin where the hair grows. Make sure to cover this up well - it's a dead give-away (waxing is best - you can live with no stubble for the few days it takes to grow back).
You cannot adequately cover up a beard or moustache. You may be able to with a latex appliance - flattening the moustache with spirit gum under it - but I've never seen it done, and if it's more than a cm or so of hair, you'll just look lumpy.
3. The Face. General Note : Women of any race are lighter skinned, slightly, than the men. This is a fact. You may with to choose a foundation slightly lighter than your skin tone - but don't go too light or you'll look ghostly in an inhuman way.
A. Forehead. Try shading at the hairline, and shading on the top bone before the temples so they "stick out" less. You may also wish to shade carefully and lightly on the bones of the forehead if they cause "brain bulge" at all, as well as brow ridges if possible.
Longish bangs will make a face more feminine most of the time, as will layers around the face. Hair makes a HUGE difference - really.
Also, if you have a high forehead, you might want to bring the wig down past your natural hairline so that it shortens it. You can use a hairlace hairpiece with natural hair, too, but these need to be custom-made.
B. Eyes. Female eyes are generally more "doe-like". If your eyes are droopy, you may want to refrain from using eyeliner on the top lid - it will make the eye area look smaller. Use a light-coloured or nude-white eyeshadow if your orbit is not very visible - and shade "slightly above the crease" of the eye and shade lightly and carefully above it - but don't use too garish a colour to do so (browns and corals and goldens are nice).
Don't use bright colours if you want to pass or unless you have experience using them. They will draw attention and closer inspection that might "out" you from passing. Don't use much colour on the skin between the orbits of the eyes and the eyebrows - it's too "drag queen" if not done well.
Do not apply too much eyeshadow close to the nose (it brings the eyes together) - stick to the outside areas, you may wish to do a little "cat's eye" "Egyptian eye" flick away from the eye to make them look farther apart. Must be very slight for everyday makeup, and perhaps in brown. You can also shade a bit with eyeshadow.
Apply concealing liquid or foundation under the eyes in the "tired circles" and the area where crow's feet would be / are.
You can use eyeliner under the eye, usually. Depending on the shape of your eye, you may want to not use a lot or any in the middle or it will make the eyes look droopy.
C. Nose. Shade down the sides of the nose, a bronzer is nice for this - I use MAC's "golden" for a lot of shading and it looks very nice. If you use theatrical cream shadow, blend well - this should not be a LOT darker, it needs to look natural.
Highlight down the center, perhaps skipping a prominent bridge.
You may de-emphasise nostrils with shading if you wish (but highlight a tiny bit to look natural). You can also take a brown eyeliner pencil to the bottom of the nostrils and shade a little tiny bit on the outside to make them look more flared if it suits your face.
Most will want to shade a little on the underside of the nose, and a little bit up (don't draw the highlight all the way to the end). Just a bit.
D. Mouth. Pick a natural colour - a blue-pink or a peach are usually good choices. Though red is classic - go for a darker red like MAC's VIVA Glam I, rather than a bright hooker red (hard to pull off and will draw attention usually in a bad way if you're trying to pass).
Get a lip-liner that matches or is slightly lighter (darker is also too "drag queen" to pass). Outline the lips in a feminine shape - don't go more than 1.5 mm outside the mouth unless the skin is very flat and your lips are TINY. It will look more natural if you keep close - emphasise the cupid's bow if you can and the reverse on the bottom lip.
Adding lip gloss (pat down after this or it WILL get on your teeth) will really plump up your lips and make them more feminine. If you get clear you can use a little on any colour lips for a nice shine.
E. Chin. Try to de-emphasise a cleft-chin. Shadow a bit at the bottom very softly to try to shorten a big chin - and at the sides of the jawline. Do not highlight unless you need to for balance.
F. Cheekbones and Jawline. If you have prominent cheekbones, either powder over these / highlight for a rounder look or work with them. Highlight on the top of the cheek bone to close to the nose (this will help make the nose look smaller), if cheek-bones are high and tellingly masculine, you might be able to work with them by extending the highlight downward - cheekbones are attractive on women, but too strong might look odd.
Blush is usually best applied to the "apples" of the cheeks in a vague triangular shape imitating a natural blush. The severe blush on the sides of the cheekbones will tend to look garish (as it does on many women).
Shade the back of the jawline especially.
G. Neck. Shade Adam's Apple (very lightly where the light hits or you'll call more attention to it). Highlight in the space between this and the cords on the neck.
A garment with a collar is best if it's especially prominent.
4. Extras. Fake nails. Not too long or they'll look garish. If they're your own - same thing. Pick a subtle colour like the typical "French Manicure" or a light pink. Push cuticles back (for some reason, men tend to not do this).
5. Body Shape. Stuffing an "old lady" full-coverage bra is best. Some Wonderbras provide a good base (I have a strapless one that holds shape well on its own). If you stuff the bra, use shreds of fabric. I have heard that rice works, too (in bags, silly). Unless you plan on being fondled, it doesn't really matter if they feel realistic - and unless they're giant and you're running a marathon, they don't need to bounce realistically - most women want a bra that makes them NOT bounce.
Don't pick a ridiculously large size. For a 34" chest, a B-cup or even A-cup is natural-looking. For 40" or larger, a C might work - and so on.
Google bra-fitting to find out what "band size" you wear - but the best results are from trying on a lot.
Bigger breasts don't make you look like more of a woman - they are harder to "pass" the bigger they are, and plenty of women aren't crazily endowed.
Waist - you may want to get a sturdy waist-shaper - they sell these many places, they look like corsets. Don't get one that's too short. A corset may be a good long-term investment, but beware of buying one cheaply made.
You may want to pad your hips if you're wearing something that shows them clearly. They sell produces for this, try lingerie shops / the Internet.
You can also "pad" the hips with a pleated skirt if your waist is sufficiently smaller (it doesn't have to be a lot - just a bit).
There are web-sites devoted to instructing one how to "tuck" the genitals so they can't be noticed. It's only necessary if you're wearing something that will show, which depends on your body - a body-shaper that extends to mid-thigh might be fine with a full skirt over it. The healthiness of tucking has been questioned - but you can research all of this via Google. Having seen some Drag Queens in tights - it can indeed be very effective.
6. Clothes. It's really up to you. If you want to pass easier, you may shoot for more neutral colours and more classic and flattering styles (jackets that extend past the hips, full skirts).
Rip out shoulder pads if you get something with them unless the garment is VERY tailored (in which case, you may want to just steer away from it).
V-line necks can work if your bra shapes the right way and the Adam's apple isn't prominent (plenty of women can wear V-necks with no sign of cleavage - breasts naturally fall AWAY from each other - pushing together is artificial.
Pointy-toed shoes will make your feet look bigger. Pick a peep-toe or closed but rounded toe shoe. High-heels will usually make feet look smaller. Only worry about height if you're iffy on passing otherwise or if you're really tall - then again, I think Uma Thurman is a GIANT, and plenty of tall women aren't afraid of towering over men in heels (though many are self-conscious and slouch, but this is unhealthy).
The average female fashion model is as tall as average man.