How to Crossdress

Two Methods:Men to WomenWomen to Men

Crossdressing is the act of blurring the aesthetic gender lines by wearing clothing traditionally worn by the opposite sex. Men can dress to look like women, while women can dress like men. While there is no right or wrong way to crossdress, this article can be used as a guide through the complicated process of switching your gender through the garments you chose to wear.

Method 1
Men to Women

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    Pick a theme. Women come in all shapes and sizes, so successfully pulling off a male-to-female gender transformation will depend on your body type and your target body type.
    • Pick a role model to emulate, somebody who has the same general body type as you—tall, short, thick, or thin. If you start from the same basic place as your role model, you'll do well. By using a role model, you will also have a pattern for walking, moving, dressing, and speaking.

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    Alter your shape. Our first impression of somebody's gender is based largely on their shape, to the point where it's almost instinctive. Guys generally have smaller hips and butts than women. Not only that, there's not much going on up front, either. So the first thing to do is fix those bits.
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    Say hello to the girls. Nothing says "female" more than having lady lumps. Entire industries, from garments to cosmetic surgery to publishing empires, have been built on the foundation of our fascination for breasts. For convincing cross dressing, this will be help bring you where you want to be, both physically and emotionally.
    • One way to do this is to purchase a bra and stuff it with either tissue paper or socks. If you're not interested in showing cleavage, this will work well. If you want cleavage as well as natural-looking bounce, weight, feel, and movement, you can purchase a breast form, which is a prosthesis you wear inside the bra or attached to your body.
    • If you're going for a natural look, don't exaggerate the size of your breasts—make them proportional to your body size, or even a little smaller.

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    Curves ahead. You want to look the part, but naturally, guys just don't have the curves that women have. It's nature, but mother nature can be fooled!
    • To achieve a more feminine look, you can use waist-cinching undergarments or corsets to achieve a more hourglass figure. You can also add padded panties, or silicon butt pads to bump the badonkadonk.
    • Tuck and tape the boys. While there is expensive underwear that can disappear your package faster than a fly-by-night delivery service, you an also do this easily and cheaply with a pair of panty hose and some tape (medical tape, not duct tape—please, for your own sake!) Visit this wikiHow article on How to Tuck and Tape for more information.

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    Contour your face. Your facial features say a lot about your gender, and there are measurable physical differences between the two. You will want to imply higher cheekbones and a smaller chin, and of course, you will want to shave very closely.
    • As women throughout the ages have discovered, the right kind of contouring makeup can create an entirely different facial look. You can create illusions that make features looks smaller or more pronounced and you can even draw focus to certain feminine or masculine traits.
    • Feminine face: To get those higher cheek bones, larger eyes, smaller noses, and bigger lips that are strong gender cues, use contouring powder and highlighter.
    • Add makeup to mask or modify your features to appear more feminine. Apply false lashes, mascara, blush, eyeshadow, eyeliner and lipstick to create the ultimate feminine look.

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    Do your hair up. While you can grow out your hair to naturally get the look of the opposite sex, you can also take advantage of wigs to create that look temporarily, and try out different looks and colors to find one that suits you. Look online at celebrities to find the right hairdo for your new features.
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    Dress the part. Get the right fit by trying on your clothes that match your figure. You don't want to buy a dress only to find out it doesn't fit with your new cleavage. Take your measurements to determine your needs:
    • Your chest is measured with the tape snug under your arms and above the cups of your bra.
    • Measure your bust across the fullest part of your bra cups. Don't pull the tape too tight—you don't want to squish things down unnaturally here.
    • Measure your waist at the narrowest part, between the top of the hipbone and the bottom of your rib cage.
    • Your hips are measured at the largest part of your butt and hips.
    • A rule of thumb when buying a dress is to use the largest of the measurements for your dress size.

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    Pay attention to the smaller details. It's more than just how a man dresses or a woman does her make up that makes them identifiable with that gender. There are dozens of little differences, red flags that signal that you are a cross dresser. If you are looking for the obvious cross-dressing look, you can skip pass these tips. If you want to look like a woman down to the smallest details, read on!
    • Exposed body hair: Men and women expose body hair differently. Waxing, using panty hose or shaving can turn a man into a more realistic woman. Eyebrows are key as well, and sculpted eyebrows will go a long way towards a convincing look. It will also be one of the more noticeable features when you're not cross-dressed, which might be a concern.
    • Nails: This is an obvious, but a sometimes overlooked detail. Give yourself a manicure to achieve the look you want.
    • Accessories: Belts, necklaces and earrings aren't unisex. Keep your accessory shopping to the women's departments.

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    Get the attitude. Being a cross dresser may be all about the aesthetics to you. If so, the following tips may not mean much. But if you want to pull off the entire gender persona, its important to have the right act down.
    • Develop the personality. Think of what kind of woman you want to be. Based on that, you may want to alter some of your basic personality traits. Try being more emotionally driven or more outgoing, and ask for things rather than demanding them. For example, say, "I would like a salad, please," instead of "I want the salad."
    • Alter your voice. For starters, you can bring the pitch of your voice up higher to convey a feminine voice. It's also important to also adopt the vocabulary associated with the fairer sex. Note that speaking in a falsetto voice will not be convincing for long. Learn to speak in a softer, more sing-song way, varying your pitch and volume more than you do when speaking as a man.
    • Walk the walk. Your movement is ingrained, and you've learned to "walk like a man" since you were a boy. Now you have to switch gears. Women tend to walk faster and use their arms more, so try picking up the pace, and engaging your arms. As the song says, "hips don't lie," so sway your hips, but don't do it to the point of exaggeration. As with all things in cross-dressing, exaggeration will not make you look more feminine, it will just make you look more like a guy wearing a dress.

Method 2
Women to Men

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    Find a role model. Find a male archetype or two to get your cues from. Using archetypes will help you with style cues, movement, attitude, and that all-important swagger.
    • Choose guys with features that are roughly similar to yours, or you'll have a hard time making the switch convincing.

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    Square it up. Whether big or small, tiny or tall, we all have a "look" that cues others to our gender. For guys, it's generally blocky and rectangular, so that's what you'll need to shoot for for the most masculine look.
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    Tuck in the twins. Everybody loves breasts, as a single night of TV viewing will quickly evidence. Unfortunately, as prized as breasts are in our culture, they're a sure giveaway if you're trying to look like a man (unless you're going for the whole man-boob look—not recommended). If you want to be convincing, the girls have got to go under cover.
    • Usually this can be achieved by wearing form-reducing underclothes that can smooth out the look. A sports bra that is two sizes too small for you, or a control top made from a cut up pair of panty hose; can give you a flatter and smoother look. NOTE: binding too tight or for too long can cause serious health problems.

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    Flatten out the curves. Guys tend to have broader shoulders, and more of a straight line between the rib cage and hips—with narrower hips in general. The goal here is to add padding to both the shoulders and waist, and to visually de-emphasize the hips.
    • Wear looser clothing to help de-emphasize curves, in general.
    • Going to the gym can create a more masculine figure by targeting specific muscle groups. Build your chest, arms and legs to create more "bulk" on the body.
    • Padding at the waist can be done to look realistic by adding bulk with extra fabric. There are prosthetic devices available as well. It doesn't take much, just enough to reduce the appearance of wider hips.

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    Contour your facial features. Women's faces tend to be smaller and rounder, with less-prominent chins and noses. You can use makeup to help mask a feminine face, but it will be more about attitude than look, if you want to be convincing.
    • Men have smaller lips, larger noses, bigger eyebrows, lower cheek bones and a more pronounced jaw line. Use contouring powder to create heavier looking features. Don't use any additional make up to add color to the face. Adding "facial hair" can make a large difference in your look, but be cautious—it won't stand up to close scrutiny. Consider adding a high-quality mustache or goatee for a more convincing look. Even men with naturally sparse facial hair can often grow those. Just don't make it look like an overgrown bush, or it will look fake.

    • Build the perfect package. If you think about a roll of quarters, you'll have the average size about right—though you will want to adjust the proportions depending on your own physical attributes. However, while a roll of quarters might give you the right dimensions, but you will look like you're permanently ready for action. Consider stuffing with a sock, or even considering a prosthetic penis. If you use a wool sock, you may inadvertently set yourself up for a typical guy cue: scratching the itch.

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    Get a haircut. Short hair on women is generally OK in 21st century culture, especially in locations where cross-dressing is acceptable, so there shouldn't be a big issue with trimming your locks.
    • Consider keeping enough length so that you can give your hair a soft look when you're out of character, and then slick it up and back when you're in character.

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    Dress the part. Men's jeans are a sure way to de-emphasize your female shape. By keeping it looser in the butt, you'll also minimize recognition from behind. In general, a looser fit in your clothes will work to your advantage. However, if you want to look more sophisticated and tailored, make sure the clothes are cut to fit a man's shape—then back-fill with padding and minimizing to achieve the right look.
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    Pay attention to the smaller details. While first impressions go a long way to establishing your identity, a lasting impression will work only if you fine-tune the details.
    • Exposed body hair. Let your leg and underarm hair grow naturally. With the exception of Olympic swimmers and competitive cyclists, guys don't shave there.
    • Trim your nails. This is an obvious, but a sometimes-overlooked detail. Give yourself a manicure to achieve the look you want. Keeping your fingernails trimmed down so that a sliver of white shows will help. Don't trim into the quick or you'll look like a nervous wreck.
    • Accessories: While lots of guys wear necklaces, bracelets, and earrings, most guys don't. Since the goal is to avoid being taken for a woman, avoid such trappings. If you do decide to go with jewelry, shop in the men's department.
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    Be the man. If you want to pull off the entire gender persona, its important to have the right "act" down.
    • Develop the personality. Think of what kind of man you want to be. Based on that, you may want to alter some of your basic personality traits. Try being more aggressive, and being direct when you want something instead of being nice. For example, to quench your thirst when dining out, say "Excuse me, we'd like some water here, please." instead of "Hi! Yes, may I please have a glass of water? Thank you so much!" For a man, it's not a question, even when framed as a question.
    • Alter the voice. Bring down your voice to become more like a man. Also speak more like a man speaks—louder, more flat-toned, and more clipped. Guys also tend to slur their words, saying "I gotta have that car," where a woman would more likely say "I must have those shoes!" It's also important to adopt the vocabulary associated with the opposite sex. Nothing is ever "fabulous," "adorable," or "precious." It also helps if you have a prominent Adam's apple.

    • Talking the talk? Now walk the walk. Slow it down. Men swing their arms less and walk slower, and keep their hips from swaying. Take longer strides, and exude confidence. Have a 'I know where I'm going' rather than a 'time to check the map again' attitude in the little things you do.

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    Put it all together. Talk the talk, walk the walk, dress the part, play the role, and be the man!


  • Most of all have fun, because it's exciting.
  • For women cross dressing as men, walk with your feet farther apart (not too far though!!). For men cross dressing as women, walk with one foot in front of the other to sway your hips.
  • Try it out. Before you go about investing in a particular look, it's best to try crossing dressing in smaller steps. For example, don't go investing in an entire wardrobe of bras before you even decide if you feel comfortable wearing them—a lot of cross dressers don't. Similarly, if you are a woman, try "padding" your underwear at home before you commit to wearing it for an entire night out, you could find it to be all too uncomfortable.
  • Get emotionally there. Cross dressing isn't just about the look, it is about the emotions that you get switching between the "feminine" and "masculine" aesthetic. If you are having concerns or feel like you need more support, try looking online for cross dressing blogs or chat rooms. This could make all the difference in your confidence as a cross-dresser!
  • Ask a trusted friend of the opposite sex to help. They can give you tips that you might not have thought of.
  • This is best to do at Halloween, then you don't get as many stares.
  • Chances are that it will take you quite a while to become convincingly opposite. Practice makes perfect.
  • For women crossdressing as men, sag your pants a little to de-emphasize your rear-end.


  • Do not rush the preparation process.
  • Do not try to overdo things.
  • Avoid exaggeration
  • Do not bind with an ace bandage

Things You'll Need

  • Makeup
  • Clothes
  • if you you are male don't have long hair, you'll need a wig, or a feminine style to your hair; if you are female then you will need a wig if you don't have a masculine hairstyle

Sources and Citations

Article Info

Categories: Gender Expression | Fashion Styles