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I wrote this article which will be part of Carollyn Olson's second "Tricks of the Trade"  book which will be released by the end of 2013.

Watch out for certain pitfalls that are easy to fall into. Just because those shoes are soooo cute and that skirt is just beautiful doesn’t meant they should be worn together. Nylons make your legs shapelier but despite Kate Middleton’s lead, they aren’t worn as much as they used to be and should never be worn with open toed shoes or casual outfits. Black nylons generally should not be worn with anything but black shoes and a dark dress. Be careful about dressing too young or trendy.



A good way to compile a series of outfits that you can call up is to take pictures of the ones that look good. When you buy a new article of clothing, play with it and see how you can dress it up or down. Often an outfit can seem good when you put it together but later when you look at the picture more objectively you how it doesn’t quite work.



Like all of these guidelines there can be lots of exceptions and finding those exceptions can be a lot of fun too. Just be sure to leave plenty of time to clean up the mess when you’re done.

Even after taking all those ideas into account it can still be difficult to know what pieces to put together. A safe place to start is with solid, neutral colors (or demim as it can be paired with almost anything). A lot of women start and end here but that can be boring and as a cross-dresser you probably want to take advantage of more feminine designs to enhance the illusion. Simply adding one fun item to any solid, neutral outfit can take it from boring to stylish. Exchange the top or bottom for one that is bright colored, patterned, ruffley, tight, or baggy. Make sure it is just one item. You can even do this by trading out the shoes for ones that are colored or patterned if you balance the color in a top or necklace of the same color.



As for shoes, in general, the height of the heel should match the dressiness of the outfit. The higher the heel the more dressy the outfit. Similarly, makeup should be less dramatic for casual and day outfits and more dramatic with evening and dressy outfits. Colored eye shadow can be very tricky and is best avoided.

While there are various reasons that men like to crossdress, the goal is usually to create an illusion that conceals the masculinity and creates an image of femininity. However doing this in a stylish way can be challenging. Some of the most fun I have is to take out all the clothing items I own and pair them in every possible combination until I find an outfit that I think works. And judging by the state of my daughter’s bedroom, she does this same thing every day.



That can be very time consuming and there are better ways of putting together an outfit. Whether planning on going out shopping on Rodeo Drive or just dressing for the mirror at home it helps to try to take several factors into consideration even if they are purely fictional. First you have to consider the season and temperature. Also, the outfit should also be appropriate for the expected activity. Will those heels still feel comfortable after an hour of shopping? One of the fun choices is to get to pick a mood; do you feel like you want to blend in, be casual, feel girly, or be a sophisticated pretty woman. Finally, the outfit should be as flattering as possibly. Be sure that none of the pieces of the outfit are obviously contradictory to another. Luckily, most things can fit into multiple categories.



Putting together an Outfit