You might want to disguise yourself as a woman for a theatrical role, a Halloween party or your own amusement. How successful your attempt will be can depend on the clothes you choose, the undergarments, makeup and even just how you are naturally built. Making good choices can help your costume or look work and make it much easier for you to pass as a woman.
Start by shaving. Depending upon your dedication to this disguise or costume, you may want to shave not only your face and neck, but also your legs and forearms. Be sure to use a new blade and shave right before dressing. Moisturize your face and neck after shaving. Do avoid scented shaving products for men. Disguising yourself as a woman is less effective if you smell like a man.
Assemble your under layer. A pair of control top pantyhose is a good start when dressing as a woman. You might also consider a snug pair of tummy control woman's underwear to help avoid any unsightly bulges under your dress. One of the key differences between male and female shape is waist definition. A good girdle can help to create a defined waist. Choose a bra in a size logical for your frame and stuff it appropriately. Your breasts should sit in the appropriate position on your chest, neither too high nor too low. Hosiery is a reasonable choice for bra stuffing. However, if you perform in drag shows or dress as a woman regularly, you might want to invest in silicone breast forms.
Get dressed. When disguising yourself as a woman, choose stylish and modern clothing. Avoid sleeveless, strapless or halter style tops. These will only emphasize the width of your shoulders. Three quarter sleeves work very well on larger frames, as do tunic styled tops. Be sure that your clothing fits your body well. Wear a heel only if you can walk in it.
Style your wig, choosing a style that suits your age and attire. Put your wig on, using adhesive to secure it if appropriate. Enlist a female friend for makeup help, or take the time to visit a makeup counter and ask for tips. Start with clean, shaved, moisturized skin. Apply concealer and foundation first, then eye makeup, blush and lip color. Generally, subtle is better, but not if you are actually trying to do drag or theatrical costuming.
Watch your manners. Sit like a lady, with your legs together and crossed at the ankle. Make sure your posture is upright and avoid slouching. Take smaller steps when walking and reduce the movement in your arms. Avoid a falsetto voice, but do speak more quietly when dressing as a woman.
Many men will need to shop in the plus size section to find the right fit. Some stores offer tall plus sizes.
Good quality makeup will do a better job of covering any potential hair growth.
Never wear foundation on an unshaven face.