Don't: What to Avoid When Starting to Crossdress

what to avoid - crossdress tips

Don't: What to Avoid When Starting to Crossdress

So, you have longed to dress as a woman and are a beginning crossdresser, but you don’t know where to start? You’ve come to the right place, since En Femme fashions and accessories are just what you need.

We’ve all been in a similar situation. Making the right decisions when it comes to every aspect of crossdressing is never easy. Finding your “desired self-image” with the right makeup, clothes, hair style, and so on can be nerve-wracking to say the least. When even the commitment to dress as a woman is so overwhelming, total frustration can cause you to shout “I give up” time and time again.

Don’t give up, even if you must take baby steps to reach your goal. The end result is always satisfying and worthwhile.

The following is a list of my recommendations of what “Not To Do” as you strive to fulfill your dream.

Don’t wear your unsuspecting wife’s clothes, undergarments, makeup, wig, or accessories. By doing so, you will inevitably leave telltale makeup or perspiration stains, among other things, on her clothing. Worse yet, you may tear a hem or damage a top or dress. If your spouse is OK with your crossdressing, ask her first. Your spouse may prefer that you buy your own clothes, so she can borrow from you.

Don’t be afraid to go out to the mall or department store in male mode and shop “for your wife” when putting together your wardrobe. Internet sales are great, but when shopping in person you can see and feel what you are purchasing and it’s a lot more fun. You may also find sales associates who are willing to help, even when you are buying lingerie.

Don’t shy away from sitting in a mall or department store and watching women. Get yourself a cup of coffee or a soft drink and analyze how they walk (especially in heels), move their hips and hands, tilt their head when taking, style their clothing, and so on. You will learn so much in no more than an hour. Then go home and practice.

Don’t buy a cheap wig, or anything cheap for that matter. Your wig should look real. At times, you can get lucky with a cheap wig or inexpensive clothing, but aim higher and look for moderately priced items of better quality.

Don’t wear too much makeup. Beard cover, foundation, eyeliner, eye shadow, mascara, blush, and lipstick are perfect. And don’t over indulge. You want to look like a woman, not a drag queen. A department store cosmetologist can be a big help as many are willing to assist in teaching you the proper way to apply makeup. Remember, our money is worth the same as any genetic woman, and a CD often spends more on product.

Don’t wear false eyelashes until you are comfortable applying them to your eyes. Remember, practice makes perfect.

Don’t be too buxom up top or too wide in the hips. You want to be proportionate to your height and weight. Always err with smaller sizes. If you want to have 38D breasts, try 36C instead. If you don’t have the money, don’t worry about buying a corset or contoured hip pads. Buy a body shaper and create your own hip pads out of sponge rubber until you know what look you want and have the money to purchase a quality corset or padding. It takes some time to be comfortable and confident when wearing a corset, while a body shaper will pull you in at the right places and give you a slimming figure.

Don’t wear outlandish clothes and colors. Dress appropriately, not necessarily for your age, but for your surroundings. You want to blend in when out and about, so dress conservatively. Think “office” styles when buying any ensemble. Skirts, sweaters, blouses, above the knee length dresses, and low heels and flats are a perfect start.

Don’t wear gaudy or over-the-top jewelry, such as earrings or rings. Jewelry is important, but make sure every item is complementary to your outfit and shoes.

Don’t buy 4-inch heels until you learn how to walk in 2-inch heels. Walking in platform or ultra high heels is not as easy as it looks. Practice, practice, and practice!

Don’t let your first time out be a downer, one where you will go home and say “never again.” Of course you will be nervous, so carefully plan, execute, and enjoy. You don’t need to go overboard. The first time out should be simple and brief. Take baby steps. Even going for a drive in your car is better than nothing. If you are really brave, go to a mall, a department store, a movie, or someplace where there are people. You have worked so hard to get ready and look as good as you can, so take advantage of the moment. Try to blend in. Remember, nobody is consciously looking for a “man in a dress.”

If you can handle each "don’t", you’ll have no problem with the "do"!


  • Tina

    I really want to out to a restaurant for dinner, I've done the drive through a couple of times, was exciting. But when going out for a real meal, how do you handle paying with a credit card? When my ID is male and and dressed and cards are "male".

  • Josh

    love the advice

  • Carollyn

    Dear Rhonda — I'm glad to be of assistance. It is so much fun to help others. Take a look at my other blogs too. Hugs, Carollyn

  • Rhonda

    I loved this article Carollyn. Very good advice.

  • Carollyn Olson

    Dear Lynne — I don't understand why a PO Box will not work. I have all my items shipped to my PO Box. Maybe Canada is different from the USA. I would check with your postal authorities. If that does not work, try having the products shipped to a friend who understands your situation. Best wishes. I know you will love the SF clothes as much as I do. Hugs, Carollyn

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