Occasionally, I get an email from someone who is just starting out with crossdressing and asks for advice on how to begin. This happens frequently enough that I thought it would good to put down some suggestions here. Please be aware that any of these suggestions may be worthy of a much longer explanation, so forgive me if some of the topics seem to be brief.

So where to begin? Much depends upon each person's situation, but I'll make a few assumptions. The first assumption is that the new crossdresser wants to present well enough to leave the house and venture out to some relatively "safe" place, such as a trans-friendly club or GLBT event. The destination is important since it implies that the crossdresser does not need to be 100% passable. The second assumption is that the crossdresser is fairly closeted, so some discretion is needed. The third assumption is that the crossdresser is financially secure enough to be able to shop at more places than just a thrift store.

In general, there are a number of important things to be concerned with, namely, hair, skin, clothes, voice, deportment, and "shape."

For hair, you should get a decent wig. Unfortunately, I can't offer too much advice with wigs as I have only wore wigs on only a very few occasions, but I will offer some. Obviously, feminine hair styles are often very different from men's hair styles, so you may wish to get a good quality wig. Don't go cheap as the wig will not look convincing. A wig will often be the single best thing that you can use to hide your identity. People can really change their overall appearance just by changing their hair. If you use tape under your wig to pull up the skin on your forehead, you will often lift your eyebrows into a more feminine arch and dramatically increase just how differnt you look. Eyebrows have a great impact on how people recognize faces, so if you are trying to be discrete, then a good wig and an "eyebrow lift" may be the way to go!

You should screw up enough nerve to go to a wig shop and try out a few. Find one that is way outside where you live so that you won't feel as if anyone would recognize you when you go. If you are not sure where to go, find out where other trans folk in your area use. A bar or club that offers drag shows is often a great place to ask people where they get their wigs or hair done, so it may be worthwhile to catch a show and talk with a few people…

For skin, the biggest issue will be covering your beard and makeup. The best thing to do is get a really good foundation that matches your skin tone. Get out to a MAC store and have them match the right color. They are very trans friendly so just tell them that you are starting out and need help. Yes, MAC cosmetics can be expensive, but they are a good value and you'll save money in the long run because you won't buy cheap stuff that you are unhappy with and be forced to replace it. Check out "My Makeup Routine" for details on how I apply my makeup. I may not be the best with makeup, but my routine should help someone just starting out.

Another suggestion is to schedule a "makeover" at a place, such as Glamour Boutique, that specializes with trans folk. You can ask them to explain to you what they are doing as they do it and you'll pick up a lot. Of course, many of these places will sell cosmetics too, so you should be able to buy the exact items needed to replicate the look. You may not have the skill to apply makeup as well as they can, but you can learn. As far as makeup is concerned, much of it is practice, practice, practice. Do your face, take a picture, wash it off. Do your face again, take a picture, wash it off. Do your face yet again, take a picture, wash it off... Go back and examine the pictures to see what worked for you. There are many cosmetics sites that offer "how to" instructions that you may wish to investigate. "Making Faces" by Kevyn Aucoin is a widely respected book which explains not only the basics of makeup application and technique but also how to use those fundamentals.

Clothes can be difficult. The most common mistake new gals make is to dress like the girls that they wish they looked like rather than dress in ways that flatters them the way there are. If you are 19, one can get away with a lot as long as you dress appropriately for the situation. If you are in your forties, then you have to deal with the masculinizing effects of age too. Just remember, don't wear something to the grocery store that you would be better off seen at a dance club.

Of course, things cost money and you may not have a lot so try to get things that are versatile so that you can mix and match items. Most crossdressers first starting out tend to buy a lot of black colored items. While every gal needs a few black items, especially that LBD ("Little Black Dress") and black is great to wear any season, your entire wardrobe should not be black or monochromatic! Grey suits with white shirts are such a guy thing. Girl, you need color! Women wear colors and so should you - but not just any and every color. Depending upon your skin tone, some colors will work well with you while others can make you look ill. Check out the book "Color Me Beautiful" by Carole Jackson to determine what colors typically work for your skin type.

Also remember to dress appropriately for the season. If it is winter, dress warmly. Even a genetic girl may look out of place if she is wearing a miniskirt and a tank top with no coat in February. In general, women wear jeans, slacks, and pants. If you want to blend into the crowd, do the same.

Heels do flatter your legs, but remember to give your feet support and use cushioned inserts. Even many hearts tends to race when they see a pair of strappy stiletto heels, remind yourself that you need to wear sensible shoes once in a while. Make sure your shoes aren't too tight OR too loose - both can cause foot pain. If you have a new pair of heels, you might want to put on a couple of strategically placed band-aides on your feet before you leave the house so avoid blisters.

When you are pulling together your wardrobe, don't forget about the accessories! Accessories will often pull your best outfits together. For example, hand bags and purses can be very important. Don't skimp on the quality of your handbag. Women take their purses pretty seriously. And pick out a quality hand bag rather than a cheep $10 bag you would expect a 12 year old girl to select. A quality hand bag will enhance your overall look a lot more than you might think. When in doubt, go for a larger handbag rather than the smaller one. In general, your purse should match the color of your shoes although this isn't a crime that the fashion police will arrest you for if they don't match.

Voice is one of the more difficult areas to master. I still don't speak well enough as a woman and that is mainly because I am not diligent enough to constantly practice. Andrea James has a great "Finding Your Feminine Voice" voice training DVD. It is well worth it. Also, to appreciate "how" women communicate (and not just talk), pick up the NY Times best seller "You Just Don't Understand" by Debroah Tannen.

Keep in kind that women are shaped differently than men, so you may need some help to get a feminine silhouette.

You should consider investing in a decent pair of breast forms. You can go "cheap" and get foam ones but in the long run, you are better with silicone breast prosthesis. You can find forms at The Breast Form Store, FantasyGirl.com, or Glamour Boutique. Also, you can do a search on eBay for good deals. I recommend the asymmetrical forms and that you stick with known brands such as Nearly Me, Classique, Mystique, and Amoena. Here is a link to a search on eBay for breast forms.

Since men do not have the same hips as women, you may wish to consider "hip pads." Fredrick's of Hollywood sells an inexpensive set of padded panties, but if you can afford them, get a pair of "Veronica" hip pads from Classic Curves International. This company that produces custom made body-enhancing foundation garments for crossdressing. These are simply the best hip pads that you will find. I have yet to find someone who has purchased "Veronica" hip pads who didn't think that they were the best she has ever worn.

I strongly recommend attending a trans conference. The workshops alone are well worth the price of registration. Workshops will vary from event to event, but you will usually find workshops on makeup, voice, deportment, hair, style, as well as more "hardcore topics" as gender theory, political activism, and relationships.

Well, I hope this helps! Any comments, suggestions, or corrections are always appreciated.