Over the past 50 years or so, gender lines in the United States have been blurred and, in some cases, nearly erased. Gone are the days of manly men and girly girls; from drag queens to bois, people are defining themselves by their psychological gender and not just their physical sex. This shift is especially evident in popular culture, as more and more models are sporting a glamorous androgynous look. In some cases, it's impossible to tell whether they are boys or girls. If you are a male who wants to look female, a few easy makeup steps will get you started.
Prep Your Face
Choose makeup colors that are flattering and appropriate for the occasion. Match foundation and powder to your skin tone by putting a little bit on your wrist and blending well. The right color will disappear against your skin. For daytime, go for a neutral look with browns, grays and other muted colors. You can go brighter for evening or an event. Men with darker skin can get away with bolder colors than their fair-skinned brothers.
Wash your face well with a gentle cleanser. Pat it dry, don't rub; this could irritate the skin.
Shave your face with a good shaving cream and a sharp razor.
Rinse with cold water and pat dry.
Apply moisturizer to your entire face, and allow it to soak in for several minutes before beginning to apply your makeup.
Create the Base
Apply foundation evenly to your entire face with your fingers or a makeup sponge. Be sure to blend well at your jawline and hairline to avoid a line of demarcation. If you have a shadow on your jaw even after shaving, you may need to use a heavier pancake or cream foundation rather than a liquid base.
Apply the darker concealer under your cheekbones and around your hairline at your forehead. Use this concealer anywhere you want to minimize, such as on the sides of your nose or around the base of the jaw. Blend well to avoid any lines.
Apply the lighter concealer to places you want to highlight, like the tops of your cheekbones. Adding some to the bridge of your nose will make it appear more slender. Blend well.
Apply pressed powder to your entire face with the powder puff, ensuring that there are no lines around your jaw or hairline.
Apply a small amount of blush to the tops of your cheekbones and blend well. Choose a blush that closely matches the natural color of your lips. Anything too dark or pale will look costume-y and fake, and all you need is a bit of a natural-looking flush.
Beginning at the inner corner of each upper eyelid, draw a line with the eyeliner pencil as close to the lashes as possible, extending the line to the outer corner of the eye. If you choose to line the lower lids, make sure the pencil is very sharp, and stay very close to the lashes to avoid a "raccoon" look.
Apply a neutral eyeshadow to your upper lids. Use a darker shadow in the crease to create definition.
Carefully apply mascara to your top lashes. Applying two coats will ensure that your lashes appear full.
Apply your lipstick. For a more neutral look, choose a color that is close to your lips' natural color, with a bit of shine. For a bolder look, go for a bright red or coral. Trace your lips carefully, and add a dab of clear gloss to the center of your mouth to make lips appear fuller.
Contouring is important, especially if you have broad features. Applying dark concealer around your jaw line and the sides of your nose will soften and feminize your face.
For a bold, in-your-face look, replace the neutral eye colors with bright blues, greens and purples.