Crossdressing 101 is the theme for this page dedicated to the beginning crossdresser. Although they may have been experimenting with dressing up as a woman has never fully dressed as one. The information on this Crossdressing 101 page is intended to get the beginner started the right way avoiding problems by addressing them up front.
If you as your male self were to stand in front of a wall with the light directly behind you would see your shadow. If you were a woman the shadow would have curved hips. To create the illusion of a women you need them too. This is accomplished with breast and hip pads positioned in the right places to create a feminine shape. I feel this needs to be done first because it is the foundation you will build upon to create that womanly look. Every piece of clothing that you purchase for your crossdresser self in the future will be based on this foundation so you need to get it right the first time. Makeup, wigs, shoes and accessories can be changed easily if needed. Changing your shape could mean that you throw clothes away or spend a fortune altering them.
I recommend gel hip and breast forms because they last forever and produce and realistic crossdressing feel. Gel pads run between $200 and $300 and breast forms from $100 to $400 depending where you buy them. If you buy gel it will probably be the last you ever buy.
The figure shape that you create with these forms will be your dress size and all of the clothing that you buy will be based on this decision so get it right. To look right it must be proportioned correctly so that you are more believable. The breasts should be large enough for a woman of your height and weight. Hips should be about the same width as you shoulders or slightly smaller. Women are more athletic today than 50 years ago so the have smaller hips. The FEMININE SHAPE FOR CROSSDRESSERS page on this site will show you how to get the correct figure.
Makeup is the next step in Crossdressing 101 for creating that feminine illusion and where the real fun starts. It is a very important step and there is much to learn if you want to look your best. There is a lot more to it than just putting it on the same stuff in the same place a woman does. The proper crossdressing makeup with in the correct shades will do wonders for your presentation.
Your foundation is the key and it must match your skin complexion or tone. That’s why they call it foundation, duh! The best way to find what you need is to have a makeup artist do it for you like the gals as MAC or Sephora. You can level with them and tell them that you want to do crossdressing. They will do your whole palette or foundation, blush, lipstick, mascara, eye shadow and setting powder.
You can also tell them that you are doing a play, Halloween or something else like that. They will know it’s a lie and they will do your whole palette or foundation, blush, lipstick, mascara, eye shadow and setting powder anyway.
Or you can guess and buy foundation that looks about right take it home to see if it matches than go spend more money to get closer to your match.
Another option is to find someone who does crossdressing makeovers for Transgendered people in your area. Some crossdressers find one where you can travel to and have them do it for you. If you go this route you will learn the WHY which, I will be covering next anyway.
WHY= Is the question of what palette goes with what skin tone?
WHY=do you put it where it goes and how do you do it?
WHY= must you need to learn contouring and what is it?
WHY = beard cover is necessary and what is it?
WHY =crossdressers need to do their makeup differently than a woman?
The crossdressing makeover artist will know all of the above. The MAC & Sephora ladies might. You can find lots of techniques on Youtube but unless you know the WHY’s you might end up looking like a clown or witch doctor!
The first challenge for crossdressing men is the beard which, must be covered unless it is mostly gray or white. Most people can get away with Pan Stick by Max Factor which is a thick cream in tube form. When I used it I made stripes in different parts of my face and the blended them together.
Once your face is all one color you can proceed with the rest of the makeup routine. Most guys need to contour in order to change the shape of the face. Contouring can eliminate the square jaw, make the face appear smaller and more oval along with enhancing cheek bones.
Unless your hair is long enough to style like a woman you will need a wig which, the style, length, and shape are very important. This can be a real challenge because for those new to crossdressing. I highly recommend going to the wig shop dressed as a woman with your makeup on before you buy a wig. You can either go to the crossdressing makeover place getting dressed and doing your makeup there possibly buying one from them. Another option is buy a cheap wig for $50.00 or so and then go to the wig shop dressed en fem with your makeup on.
The wig sales person will match your foundation tone to the wig color to get something that compliments your face.
Until recently I never wore a short wig in public after trying some on 30 years ago hating the look on me. My wife insisted I try a new one she bought in December telling me she thought it would be great. To my surprise I loved it! Although short it is also tall which along with my long earrings made my face appear thinner and more feminine. So much for the old dog new tricks thing, its all about illusion.
So now you have your makeup, wig, pads, and dress all put together you will need some shoes and I recommend ballet flats which are popular now. Take your men’s shoe size and go up two sizes so if you wear a 10 in men’s you should be pretty much a 12 in women’s. You can buy them online and I would advise cheap ones to start with elastic if possible until you can have your foot measured by a professional. A shoe stretcher is also a good investment.
Crossdressing 101 in high heels are where we all go and you have two options. Buy 3 1/2 inch stiletto’s and practice walking at home until you are good at it or, start with 1 1/2 inch and work your way up. The 1 1/2 inch heels will not be a waste because you will probably use them for shopping later on. Most women do not go shopping in 3 1/2 inch heels in the mall.
Finally we have earrings, bracelets, necklaces and pins accessory jewelry. You can play with this but large jewelry makes the area you wear it on look smaller which is good. Less is more though when it comes to quantity with one ring on either hand not one ring per finger. Watch women that you come in contact with and see what they do. A couple of thin bracelets worn together is fine but if you wear a watch no bracelet on that wrist.
You are all set.
Be safe & have fun!