Dressing the Part
Get a wig or style your hair. If you have long hair already, then you can just style it. If your hair is short, then you may want to get a wig to enhance your feminine look. When you are choosing a wig, make sure that you purchase one that is high quality if you want your look to be more convincing. A poor quality wig may not look as good. If you are dressing up for a drag show or play, then you can go with an over the top wig, such as something that is ultra-long, styled like a bee hive, or dyed an unnatural color. If you just want to see what it feels like to dress as a girl, then try curling your hair, using a flat iron for a pin-straight look, or braiding your hair. Long hair will help you to look feminine and it can also provide some coverage from masculine features such as a square jaw, but having long hair is not absolutely necessary if you are just dressing up to see how it feels. If you have short hair, then you can also try styling it in a feminine way. For example, you can use mousse and curl the longer pieces, or wear an accessory, such as a headband or barrette.
Put on makeup. Makeup can help to accentuate your features and give your face a more feminine appearance. If you have never worn makeup before, then you may need to watch some tutorials on how to apply it. Try checking Youtube for some basic makeup application tutorials. If you just want to get a feel for what it is like to wear makeup or if you want to try to pass as a girl, then stick with a light layer of foundation, some light eye shadow and mascara, and a nude or pink lipstick. If you want something more dramatic, such as for a drag show, then you can put on a heavy layer of foundation, black eyeliner, fake lashes, and some bold red lipstick.
Wear women’s clothing. Wearing women’s clothing is an essential part of looking like a girl. Lots of girls wear unisex clothing, such as pants, jeans, and t-shirts. However, dresses are your best bet for drag shows because they are flashier. If you just want to get a feel for what it is like to dress as a girl, then wearing a dress or a skirt with a girl’s top will give you a better idea. Choose a style that flatters you and shows off your best features. For example, you can choose a short skirt if you want to show off your legs, or a sleeveless top if you want to show off your arms. If you are going for an exaggerated look, such as for a drag show or theater production, then you might want to choose something flashy, ultra-feminine, or elaborate. For example, you could go with a sequined dress, a fluffy tulle skirt, or a hot pink evening gown. If you are interested in dressing as a girl to pass as a girl, then try to choose clothing that is in style. Wearing current trends may help make it easier for you to pass as a woman.
Add some accessories. Earrings, necklaces, bracelets, scarves, and other accessories can help to enhance your feminine look. Choose an accessory that complements your outfit and that makes you feel pretty. If you are dressing up with the intention of trying to pass as a girl or see how it feels, then you could go with a simple pair of pearl earrings or a dainty gold necklace. If you are going for a more dramatic look, such as for a drag show or theater production, then go for some long dangling earrings, a long glittering costume jewelry necklace, or a lots of bangle bracelets.
Slip on some women’s shoes. Shoes are an essential part of your look. Select some women’s shoes that go with your outfit and that you will feel comfortable wearing. High heels are ultra-feminine, but they can be difficult to walk in. You will probably need to practice walking in them before you go out in public. If you are dressing up for drag or a play, then high heels may provide the most dramatic effect. Just make sure that you can walk in them without falling! If you are experimenting with women’s clothing because you want to see how it feels or possible pass as a woman in public, then try starting out with some ballet flats, some low heel dress shoes, or a fashionable pair of sandals. Make sure that your toenails are painted if you will be baring your toes.
Achieving a Feminine Look
Shave facial hair, legs, and armpits. Getting rid of excess facial hair, armpit hair, and leg hair is crucial when dressing as a woman. Having visible facial hair can be a dead giveaway, so make sure that you give yourself a close shave before you start making the transformation. If you don’t want to shave your armpits, then just make sure that you are wearing something that covers them completely, such as a long-sleeve or ¾ length sleeve top. If you don’t want to shave your legs, then you can also go with some opaque tights. Wear two pairs for extra coverage.
Tuck your penis. Tucking your penis back is an important part of passing as a girl. To tuck your penis, pull it back towards your buttock and between your legs. Then, put on two pairs of form-fitting panties to help keep it in place. Another option is to use a gaff. You can buy or make a gaff. To make a gaff, cut the elastic waistband off of a pair of pantyhose and then cut the top off of a sock. Thread the waistband through the sock so that the sock is centered. To use a gaff, slip your legs through the two openings in the elastic and pull it up like a pair of underwear. As you do so, tuck your penis back. Then, adjust the gaff as needed and put on your panties. The gaff will help to keep your penis tucked back.
Put on a bra. Wearing a bra is an essential part of looking like a girl. Choose a bra that fits around your chest comfortably. Measure your chest around the widest part to see what size bra you will need. For example, if your chest is 38 inches around, then purchase a bra that is a size 38. The cup sizes are lettered, such as A, B, C, D, etc. A is on the smaller end while a D cup is on the larger end. You can choose any cup size you like, but keep in mind that choosing a large cup size may make it hard to fit into some clothing. To play it safe, go for a B or C cup. However, if you are dressing up for a drag show or as part of a play, then you may want to go for a larger bra size. You will also need to stuff the cups. You can stuff the bra with socks, tissues, balloons filled with a few ounces of water, or special silicone bra pads.
Wear slimming undergarments. Wearing slimming undergarments or shapewear can help you to get a smoother curvier figure. These garments can also help to taper your waist, which will help to make you look more feminine. Try wearing a corset or girdle, a pair of shapewear shorts, or a pair of pantyhose with a high waist.
Consider wearing hip or butt padding. If you don’t have much fat on your hips or buttocks, then wearing a padded undergarment or adding padding to your undergarments can help you to achieve a curvier look. You can purchase pre-padded undergarments or just slip some padding into your underwear or pantyhose. For a drag show or play, you may want a more exaggerated figure. Try using more padding or even a pillow to create the appearance of curvy hips and big butt.
Behaving Like a Girl
Practice your walk. While there is no one way to walk like a girl, you may want to practice walking in a more feminine way. Instead of taking straight, hard strides, try to walk with a bit of a sway to your hips and lightness in your step. If you are just trying to experiment with what walking like a girl is like, then just aim for some slight movement in your hips as you take each step. Unless you are going for an over-the-top walk, such as for a drag show, don't place your feet directly in front of each other as this can make your walk look too exaggerated.
Sit with your ankles or legs crossed. A masculine way of sitting is with legs spread wide and arms out to take up more space. Instead, keep your knees together and your elbows in close to your body. You can cross your ankles or cross your knees if you feel comfortable doing so. This seated position will help to give you a more feminine appearance. You can also fold your hands on your lap or place them gently on the table in front of you. Try not to slouch while sitting. Instead, keep your back straight or lean forward and rest your elbows daintily upon the table.
Adjust your voice. Women tend to have higher voices than men and this can give you away as a man dressing up like a woman. If you have a deep voice, then you may want to practice speaking at a higher octave. However, keep in mind that some women have deeper voices, so try not to feel self-conscious if your voice is a little deeper than some other women’s voices. If you are dressing as a woman for a drag show or play, then you can either use your normal voice or go with an over-the-top girl voice.
Smile and laugh often. Women tend to smile and laugh more than men. Smiling and laughing more often can help you to appear more feminine, so try to smile and laugh a lot. Unless it is part of your drag show or character, you don’t need to wear a big grin constantly or laugh all of the time. If you are just trying to get a feel for more feminine mannerisms, then try to smile and laugh a little more than you usually would. If you are having trouble doing a feminine laugh, try a soft giggle instead. Make your voice a little higher, but don't make it sound like Minnie Mouse.
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