How to Crossdress

Co-authored by Joanne Gruber

Last Updated: January 21, 2023 References Approved

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. This may be done by people who enjoy cross-dressing periodically as well as those who choose to adopt an identity as the other gender. It can also be handy for people such as actors who may be called upon to play another gender in a role. 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 choose to wear.

Method 1

Method 1 of 2:

Men to Women

1
Pick a role model. Successfully pulling off a male-to-female gender transformation will depend on picking a feminine body type to emulate. Women all have feminine curves, but differ in how it is presented. A petite gymnast will be different than a voluptuous vamp, which will also be completely different than a sweet little old lady.
- When picking a role model to emulate, it is easier to pick a feminine figure who has the same general body type as you.
  - Marilyn Monroe, for example, is a good example of a woman with an hourglass figure, not particularly thin, and medium height.
  - Portraying Brienne of Tarth on Game of Thrones can use a more muscular build.
  - Of course, accuracy may not be the point. If dressing for comedic effect, feel free to go for the exact opposite. An example would be putting a large muscular man in a fairy costume.
2
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.^{[1]
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Research source}
- 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 cheekbones, 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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3
Accentuate your bust. Entire industries, from garments to cosmetic surgery to publishing empires, have been built on the foundation of our association with breasts and femininity. For convincing cross dressing, this will 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^{[2]
  X
  Trustworthy Source
  BreastCancer.org
  Patient-focused nonprofit organization providing resources for those affected by breast cancer
  Go to source}, which is a prosthesis you wear inside the bra or attached to your body.
- If you're going for a natural look, avoid exaggerating the size of your breasts—make them proportional to your body size, or even a little smaller. Too much bust actually detracts from a natural appearance.
4
Draw in the waist. The contrast between the waistline and hips promotes a feminine look.^{[3]
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Research source} While some styles downplay this look (such as flapper dresses) drawing attention to a smaller waistline helps the overall effect.
- Waist-cinching undergarments or corsets can help to achieve a more hourglass figure. You can also add padded panties, or silicone 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!)^{[4]
  X
  Research source} Visit this wikiHow article on How to Tuck and Tape for more information.
5
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.
6
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.
7
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 past 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 pantyhose 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.
8
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. In reality, women have all sorts of behavior patterns--but certain ones are emphasized in females. Women are taught to be less aggressive, for example. They are also allowed to be more emotional than male counterparts.
- For example, a woman would be more likely at a restaurant to say, "I would like a salad, please," instead of "I want the salad."
- Women tend to show more emotion. Men are generally taught to avoid a lot of visible emotion, while a woman tends to be allowed to.
- 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. Men and women often walk differently,^{[5]
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  Research source
  www.dtic.mil/dtic/tr/fulltext/u2/a597428.pdf} and a lot of it is taught by culture. Your movement is ingrained, and you've learned to "walk like a man" since you were a boy. Women have to learn to walk in a feminine way, which emphasizes grace rather than power. As a man, you have to switch gears.
- Practice walking in heels. Nothing looks less feminine than tottering on high heels. Even if you do not go out in public in heels high heels teach balance, smaller stride, walking softly, and a feminine gait. Practice going up and down stairs especially. Being fully proficient with heels means being able to not only walk, but dance in this type of footwear.
- Women often walk faster and use their arms more, so try picking up the pace, and engaging your arms. Arms are soft, not hard and stiff.
- As the song says, "hips don't lie," so sway your hips subtly, but don't do it to the point of exaggeration.
- Be careful to walk with gentleness. Men are allowed to clomp down the hall and pound downstairs in a way that women are not. Women are taught to walk more carefully with a grace. Walk up and down stairs with a skirt, and keep in mind a woman cannot bring her knees up very high.
Note: As with all things in cross-dressing, over- exaggeration will not make you look more feminine, it will just make you look more like a guy wearing a dress.

Method 2

Method 2 of 2:

Women to Men

1
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.
2
Tuck in your breasts. Breasts are a giveaway if you're trying to look like a man. If you want to be convincing, they have got to go undercover. ^{[6]
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Research source}
- 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 and/or trouble breathing.
3
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.
4
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 cheekbones and a more pronounced jawline. Use contouring powder to create heavier looking features.^{[7]
  X
  Research source} Don't use any additional makeup 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.
5
Get a haircut. Short hair for all genders is perfectly fine in 21st-century culture, especially in locations where cross-dressing is acceptable, so there shouldn't be a big issue with trimming your locks.
- If for whatever reason you want to keep your hair, use a short-haired wig.
Tip: 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.
6
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.^{[8]
X
Expert Source

Joanne Gruber
Professional Stylist
Expert Interview. 30 July 2019.} 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.
7
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.
8
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.
9
Put it all together. Talk the talk, walk the walk, dress the part, play the role, and be the man!

Expert Q&A

Question

How can a girl dress like a boy?

Joanne Gruber
Professional Stylist
Joanne Gruber is the owner of The Closet Stylist, a personal style service combining wardrobe editing with organization. She has worked in the fashion and style industries for over 10 years.

Joanne Gruber

Professional Stylist

Expert Answer

Wear clothes that are oversized to go for a more androgynous or masculine look.
Question

If I cross dress, does that mean I identify as the opposite gender?

Heather Kenyon-Haff

Top Answerer

It depends how ''you'' feel about it. Some cross-dressers just like dressing like the opposite gender for fun, or because it feels good to do it once in a while, but they do not want to be the opposite gender and like being the gender of birth. For others, it is the start or the expression of wanting to be a different gender. Just putting on the clothes does not mean you are declaring a gender.
Question

If I am very tall and have broad shoulders, do you think it is possible for me to pass for a woman?

Community Answer

Yes. Wear clothing that has larger shoulders, and stay away from tank tops and spaghetti straps. If you have longer hair or use wigs, have your hair cover your shoulders.

Warnings

Do not rush the preparation process.

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Do not bind with an ace bandage.

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