How to Make a Man Dress Like a Woman

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Sometimes a boy wants or needs to dress like a girl. Whether it's for an acting role, just for fun, gaining a new perspective, or adopting a new lifestyle, a boy can easily dress like a girl. With a little preparation, the right outfit, and stylish makeup, any boy can look like a girl.

1
Make sure he wants to do this. You should only dress him up if he thinks it's a good idea. He should be comfortable and relaxed about the idea.
- Don't take any photos or videos without his permission. If you do take them, never share them without permission. This counts as a betrayal of trust. Double-check with him before taking or sharing pictures or videos.
- If he doesn't think it would be fun, then let it go. Maybe another boy would like to dress up.
- Double-check each step of the process with him. For example, if he's scared of the tweezers, tell him that he can skip having his eyebrows plucked.
2
Shave his legs, armpits, and face. For a boy to dress like a girl, he needs to have no leg, facial, or armpit hair. Have him take a shower and shave his legs, armpits, and face. If he doesn't want to do it himself, have him sit on a chair while you gently shave him.^[1]
- Spread shaving cream onto his legs, dip a razor in a bucket of water, and then save the hair off of his legs. Dip the razor into the water after each pass of the razor on his legs to prevent cuts.
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3
Shape his eyebrows. Girls shape their eyebrows to achieve a natural arch without any stray hairs, so shaping the boy's eyebrows will help him look feminine.^[2]
- Use tweezers to pluck stray eyebrow hairs or use face wax to wax the eyebrows into a natural arch.
4

Put girl's deodorant and perfume on. The scent of deodorant is different for boys and girls. Get a deodorant sold for girls and have the boy wear it. You should also have the boy wear a perfume meant for girls to get him smelling like a girl.

1
Find an outfit that fits well. Girls tend to wear clothes that are more form-fitting so you need to pick out an outfit that fits the boy well. Choosing a dress or skirt for the boy to wear will make it easy to distinguish that he's dressing like a girl.
- Some boys have very broad shoulders so finding a dress that fits him right might be hard. If the boy has broad shoulders, consider putting him in a skirt and shirt to get a better fit.
- If you choose to have him wear pants, it would be a good idea to have him wear skinny jeans with boots. This look is a popular style with girls.
2
Pick complementary colors and styles. The shape of his clothing can impact how others view him when they look at his body. Get a more feminine shape by using clothes and their colors to accentuate areas of the body.^[3]
- Wearing dark colors around the waist provides a slimming effect to create an hourglass look.
- Pick v-neck or lower cut tops to provide a more girly style.
- Florals and prints can give a feminine look.^[4]
3
Add accessories. You can add different types of accessories to the outfit to complete the look. Accessories are an important part of a girl's outfit, so adding accessories will give an authentic look to the boy's outfit.
- Jewelry like necklaces, bracelets, rings, and clip-on earrings will add a feminine touch to the outfit.
- Wearing colorful clothes and a lot of jewelry can make a person look more feminine.^[5]
- If the boy is wearing a dress or skirt, you can have him wear tights to add color or design to his look.
4
Select feminine shoes. The shoe style is important when trying to dress a boy like a girl. If you want to make a boy look like a girl, he needs to wear shoes that are feminine.
- Shoes with heels are a great choice. There are dress shoes and boots that have heels. Choosing a shorter heel is a good idea if the boy isn't used to walking in heels yet.
- Fashion boots are also a great choice for dressing a boy as a girl.
- Pointed toe flat shoes can also give a feminine appearance.^[6]

1
Grow long hair. Boys who enjoy dressing like girls often grow long hair to accommodate lots of different hairstyles.
- Curl his hair to add more volume.
- Blow-dry and style his hair after a shower.
- He can wear a low ponytail if he wants to dress like a boy.
2
Cut his hair in a flowy style. Get a haircut that incorporates soft waves to soften and feminize the face.
- Haircuts with sharp angles may make his face look more angular and rigid.
- If you choose to dye his hair, pick a color that compliments his skin tone. Light colors are best for cool skin tones, darker colors compliment warm skin tones.
3
Accessorize his hair. You can accessorize his natural hair with hair clips, bows, and headbands to add a feminine touch to the outfit. Brush his hair and sweep the front to the side with a girl's hair clip to make his hair look like a girl's pixie cut.
- Hair clips, headbands, and bows are a great accessory to add to the boy's hair.
- Put ribbons or barrettes in his hair to look more feminine.
4
Put on a wig. If you want him to have longer hair, he can wear a wig. Choose a wig that is close to his hair color to make it look more natural. Style the wig in any style you like.
- Wigs are a good way to create a total transformation in his look.

1

Apply foundation and powder. Find a foundation color that matches his skin tone and apply it evenly to his face. Apply a matching powder over the foundation to finish the base of the makeup.^[7]
2
Put eye makeup on him. Eye makeup will help accent his eyes and make them look bigger. Eye makeup is a great way to make a boy look more feminine.^[8]
- Apply eyeshadow on his eyes to accentuate his eye color. Consider using two or three colors to blend onto his eyelid to make his eyes look bigger.
- Use eyeliner to draw a line at the base of the eyelid. This will accent the eyes and give a finished look to the eye makeup.
- Finish with mascara on his eyelashes. Use black mascara if he has dark eyelashes and brown mascara if he has light eyelashes. For a fun, festive look you can use colored mascara, like blue or purple, to make his eyelashes pop.
3

Add blush to his cheeks. Blush is a great addition to dress a boy like a girl because it makes the face look more feminine. Apply the blush to the apples of his cheeks and his cheekbones.
4
Finish with lipstick. The finishing touch to makeup is adding color to the lips. You can line his lips with lip liner and then fill in the rest with lipstick.^[9]
- Red, Pink, and Neutral colors are good choices to pick for his lipstick.

1
Encourage him to speak in a higher register. Even if he looks like a girl, a voice that sounds like a male's will be easily recognized as a male.
- Tell him to practice speaking in a higher tone to make himself sound more feminine.
- Record him speaking so he can hear what he sounds like.
2
Have him practice walking in a feminine manner. A feminine walk will help make the look of dressing like a woman appear more natural.^[10] Women tend to walk more elegantly and keep their knees and feet closer together than men do.
- His feet should pull him forward instead of storming ahead head first.
- Have him move his hips as he walks; let his hips lead his legs to engage his whole body as he walks.
3

Help him adopt female mannerisms. Become more sensitive to the interactions he has with other people to make the interactions more feminine. Acting like a girl can often have as much mental impact as dressing like a girl in terms of how an individual is observed.^[11]

Add New Question

Question

What happens if I go to a wig store and someone asks me why I'm getting the wig?

That's probably not going to happen, but if it does, just tell them you're buying it for a costume and they probably won't bother you further.
Question

How do I dress up like a boy if I have to wear a bra?

Marian Andersen

Community Answer

Bind your breasts with tight wrappings or wear a tight sports bra. Also you could wear a very loose-fitting top.
Question

How do I hide my penis when I wear jeans?

You could always tuck it between your legs. There are tucking devices you can buy online or at specialty stores.
Question

I'm an 11-year-old transgender boy. How do I make myself look like a boy?

Looking like a boy involves many aspects. Wear your hair short, put on boyish clothes in dark colors, take daily multivitamins and sleep 8 - 10 hours per night to help you grow as tall as possible, and work out to build muscle. If you can, get your doctor to prescribe puberty blockers so that your body won't become feminine. (As you get older, you can begin testosterone therapy to help you look like a man.) Also work on your voice and your body language. Stand tall, walk confidently, and let yourself take up space. Check out our gender expression articles for more advice.
Question

Is it better to wear dresses or pants if I'm trying to disguise a man as a woman?

It depends on the body type. Have them try on a few different outfits and see what looks best.
Question

How do I dress up like a girl as a boy at a pool?

You can try wearing a girl's bathing suit and tucking or taping (using medical tape) your penis between your legs, but this might not work.
Question

What could a boy do to have girlish legs, and can a boy use Cutex?

You can shave your legs to make them look more girlish, and yes, anyone can use Cutex.
Question

How do I fit my tights with my skirt as a male?

Tuck your penis in between your legs and slip on tights. Make sure the skirt is longer than a mini, you don't want mishaps showing you up.

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Find clothing and makeup colors that match or coordinate with his eye color.
Teach him how to walk comfortably in heels to naturally look like a girl.
Have him put lotion on after you shave him. His legs might be a bit dry from shaving for the first time.

Thanks for submitting a tip for review!

Some boys may have mixed feelings about dressing as a girl. Talk to him openly about how he feels or make sure he has someone to talk to if he needs it.

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To dress up a boy like a girl, focus on making his appearance more feminine and picking out an outfit to suit his new look. First, shave his face, legs, and armpits so his skin looks smooth. Put on a deodorant and perfume designed for girls, which will help him smell like a girl. Then, pick out an outfit that's more form-fitting than typical male clothing, like a skirt or dress. If you choose a skirt and a top for him to wear, go for tops with lower necklines for a more feminine look. Add accessories to his outfit to give it an extra edge, such as a bracelet or tights. Remember to pick out feminine-looking shoes, like high heels or a cute pair of boots, to complete his look. For tips on how to style your hair to look like a girl, keep reading!

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How to Make a Man Dress Like a Woman

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