How to Cross Dress


When learning how to cross dress, you'll first need to experiment with the styles of clothing that work for your own body shape or the body shape you create with breast forms and butt pads. Wrap dresses and A-line skirts will accentuate an hourglass shape, for example. Corsets and waist-cinchers can be the undergarments of your dreams if you need a little extra help getting that ideal womanly shape.

Steps for Learning How Cross Dress

Men's body shapes come in several shapes just like women's do, so before you begin, check out women's style guides to find out what clothing styles will work best with your figure. If you're a ruler shape, for example, you'll want to play up your features differently than a spoon or apple. You'll probably want to add padding to some areas rather than learn to disguise your hips and thighs with A-line skirts or get rid of your muffin top with mid-rise pants and a flowy, voluptuous shirt with an empire waist.

1. Find the Right Fit

How tall are you? For women, over 5'8" is considered Tall while under 5'4" is considered Petite. If you have mile-long legs, you may want to check out the Tall sizes. Sometimes this will require shopping online. If you're on the shorter end of the spectrum, you'll often have good luck in department stores.

Another body factor to consider is whether you need Misses or Women's clothing. Misses typically run smaller while Women's clothing has more room in the hips and waist. Until you're comfortable choosing the right fit, it will take trial and error to find out which styles you can wear from Misses and which styles are best when they come from the Women's sections. You may find that you need to mix it up rather than shopping in just one section of the store every time.

2. Create Curves

For the most believable final result, you'll need to fill out your clothes with curves. You can create an hourglass figure with breast forms and hip and butt pads so that you can fill out those dresses, skirts, and tight tops with confidence. You can make your own breast forms and even your own hip and butt pads if you want a custom fit and like to create things.

Breast forms and padding are available for purchase, as well, so if you don't have the time, energy, tools, or skills to create your own curves, it's not a problem.

3. Master Moving as a Woman

When walking (practice in your heels for a while before stepping out of the house!), make sure you swing your hips and rotate your shoulders while keeping your legs close together. It sounds difficult and it may take some time to get into the flow of things, but it will make a difference in whether your feminine ensemble, from wig to sassy sandals, looks legit. Men tend to keep their bodies more rigid than females when they walk, and they walk with their legs farther apart.

4. Complete Your Look with Hair and Makeup

Without makeup, hair, and movement, learning how to cross dress is only halfway done. Contouring and highlighting will be your friends, especially in the cleavage department, but also to fill out masculine angles of the face and re-sculpt a more feminine look. Makeup is another area that will take trial and error; finding the right colors for your skin tone and hair color can take time.

  • Vanessa Law of recommends two things: Kevyn Aucoin's ''Making Faces'' and practicing every day, even in guy mode. A quick tip for creating the appearance of cleavage is to use a matte neutral or cool shade of brown shadow or blush that is slightly darker than your skin tone to draw a Y-shape on the chest, slightly curving out the upper arms of the Y to create the illusion of roundness there. On what would be the roundest part of the breast, apply a lighter, shimmery color. This will make the area appear to stand out further than the rest while the darker, matte shade seems to recede.
  • The Crossdresser Heaven blog also offers tips for choosing the right wig to reflect your personality. For example, if you're fun and bubbly, you'll do well in a long blonde wig. Prefer to retain some mystery? Try a brunette wig. If your temper is likely to flare at any time, you know to opt for a fiery red wig.

Use Cross Dressing Resources

Today there are more resources than ever before for members of the cross dressing community. A few resources to check out include:

  • You can shop for everything from makeup to skirts here, plus pick up a few tips along the way.
  • Crossdresser Heaven: Learn everything from how to do your makeup to where to buy your shoes and clothes.
  • YouTube: YouTube can teach you makeup tricks and even show you cross dressing transformations complete with detailed tips and tricks to make your look flawless from head to toe.

Whether you want to cross dress in the privacy of your own home or are ready to step out as a woman, knowing what to wear and how to wear it can help you feel confident and comfortable in your look.

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How to Cross Dress