Say Yes to a Dress! Get Started Crossdressing!

Angela having CD fun.

Are you a guy who has had a fascination for as long as you can remember with the idea of dressing like a girl? Maybe you hid it for years and enjoyed manly activities that you also liked. But you didn’t like bowling, or playing the guitar, or video games, or sports as much as thinking about wearing hose and stiletto heels. The manly activities that you were expected to partake in were satisfying but in the  evening while in your bed your head was filled with fantasies about going out and being accepted as a girl. If that’s the case then you are a crossdresser.

Crossdressing is about the clothing — and the role. Crossdressers are fascinated with wearing dresses, skirts, high heels and all the other attire that is assigned to the femme world. For many, also being able to act out feminine behavior in a public setting is very satisfying. A crossdresser doesn’t want to be a woman and live as a woman 24/7. Having male genitalia doesn’t upset them. They have a masculine side and a feminine “hobby.” (It can get complicated in some cases but we’re keeping it simple for this article.) Most want to live normal dude lives, and be able to dress and act as women when they can. That may be in the privacy of their home, or a hotel room, or out in public at a CD friendly bar or club. Some love to go to the mall while dressed and shop for more feminine clothing to wear. But the feminine side of a crossdresser is as real as the masculine side. Once they begin to develop “her” she can be either a full personality that’s totally different from their male personality, or a feminine aspect of their male side.

Every crossdresser relates to the drive to emulate femininity in a slightly different way. Many get a sexual thrill from wearing women’s clothes. This is not uncommon for those just starting to explore crossdressing. For some that sexual component remains their main focus, while for others the sexual thrill becomes less front and center as they begin to dress up more often and become social. It remains as a turn on but one that can be called on when being turned on is appropriate. For most the act of dressing up makes them feel sexy at least. Wearing a tight stretchy dress and spike heels is going to make anyone feel more sexy than wearing a pair of baggy jeans and a flannel shirt.

Here at TGForum we consider crossdressing to be under the transgender umbrella. Crossing the gender border part time counts as being trans. That is somewhat at odds with the popular perception of the trans condition, which is of a person born with certain genitalia who feels more comfortable and authentic living in the opposite of that birth gender. There is plenty of information on our site for full time trans people. This post is for crossdressers.

If you’re reading this post then we can assume that yes, you’re already interested in dressing like a woman. Maybe you’re already doing it secretly. Or maybe you’ve even come out to some friends who accept you being a girl for fun on Saturday night. In the 21st century, for all the blow back and controversy over the recognition of the existence of trans people, anything can happen. Many members of the public will be cool with a male friend who likes to dress up. You’ll have to feel out your friends on that. For the sake of this post we’ll assume you’re starting out from square one. Before we start your journey into feminine expression keep in mind — crossdressing is FUN! If it makes you paranoid or gives you feelings of guilt you should deal with those feelings before you continue. A counselor who understands trans issues could be helpful.

What’s First?

Dresses in a 1962 Sears Catalog.

Dressing like a woman requires one main thing first — women’s clothing. That means you’re going to have to determine your correct sizes and buy some. In the last century men who wanted to wear lady’s fashions would use the data found in the Sears Catalog. In modern times we use Wikipedia. Click here to find information on the nine different women’s clothing types. (U.S. sizes.) Their charts will help you determine if you can wear Misses, Juniors, Women’s/Plus or Tall. Most CDs will not be wearing Miss’s Petite size clothing but if you have the advantage of a small physique, you go girl! Keep in mind that clothing sizes vary by manufacturer as well as by type. Generally a large Junior dress will fit on my body and a size 10 in Misses. But with some manufacturers or styles I need an extra large Junior or a size 12 Misses.

Measuring Yourself

The proper tool for the job.

The Wikipedia chart says that a size 12 Misses’ dress fits a 36.5 inch bust, a 30 inch waist and a 41 inch hip. To measure your bust you first have to create one. This can be done with a bra filled with anything from pairs of socks to silicone breast forms (that you picked up online at The Breast Form Store. Also a good resource for getting that bra and other lingerie sent discreetly to your home They have sizing info on their site). Use a tape measure, (not a steel tape measure from your workshop) which you can buy at any fabric or sewing store, and measure your bust at the most protruding spot. Your waist is located just above your navel, not down at your navel. If you are using a bodyshaper or cincher to pull in your waist, measure with that garment on. Your hips should be measured at the fullest area. If you are planning to wear padding for your hips or butt you should have that on when you take the hip measurement.

If you find you wear a size 12 dress then you may wear a size 10 or 12 skirt. Normally, since males usually have larger shoulders than females, you may wear a size larger than your dress size in a tailored blouse. Depending on your body, how you pad and cinch, you will have to determine which sizes work best. A good way to do that is, once you have your measurements, go to a thrift store such as the Salvation Army or Goodwill and pick up a few very cheap skirts and tops with a variation in sizes. Try them on with your undergarments and see which fit best.

Clothing that is sized as Small, Medium, Large, and Extra Large should also be checked out this way. Sometimes a Large top will fit just fine and with other tops you may need the Extra Large.

What About Shoes?

Women’s dressy, sexy shoes are very different from men’s shoes. First of all they are impractical, tilt your hips forward, squeeze your toes into a point, and make your butt protrude. Which is why they are so sexy. Women’s shoes you can wear are generally one size larger than your male shoes. If you wear a size 9 men’s shoe you should be able to wear a size 10 women’s shoe. (U.S. sizes.) Some people can wear just a half size larger. The rule on shoes is — don’t try to squeeze into a shoe that is too small just because you think it’s sexy. You will not look sexy when you hobble into the club suffering from severe foot pain. Get the right size and practice, practice, practice. Start with a lower heel and work up to those extreme spike heels you covet. Payless Shoes and Famous are good places to pick up your first women’s shoes. They have sale and clearance shoes around $5 to $15 that you can practice in around the house. (Home from work? Hop into those pumps.) Once you’ve mastered the 4 inch stiletto — with no ankle wobble — you can invest in more expensive shoes. A woman who walks with poise and confidence in high heels is always attractive.

That’s the basics of women’s clothing. Of course there is an infinite variety to women’s fashion and as you dress more you will begin to develop your own style. You can be conservative in tailored dresses, hose and three inch pumps, or you can be Boho and wear colorful print dresses with handkerchief hemlines accessorized with hand crafted strands of beads and wedge heel sandals. Look around at women you find attractive. Read fashion magazines and see what styles you are interested in. Male bodies need help to look right in women’s fashions. As long as you are not too pumped up and large shouldered you should, with some work, be able to find the styles that look best on you. Of course you can wear any fashion look you like, but wearing one of those bare shoulder tops that are the current trend will not be as attractive on you if you have large shoulders as it is on a slim model. We all desire to look sexy and svelte but not all of us are. Do what you can with what you have and look for the fun in crossdressing.

This post has only scratched the surface of how you enter the world of crossdressing to become a confident feminine person having a good time in the real world. There is so much to learn, practice and perfect. I’ll try to get into some of the other areas to help you on your journey in future posts. If you have any comments or questions let me know by using the Comment area below.

For more tips see our CD 101 post from 2015.

Tags: crossdressing, fashion, featured, opinion, style

Category: Transgender Body & Soul, Transgender How To, Transgender Opinion