Crossdresser Heaven

What to wear the first time you crossdress

Crossdressing for the first time

Crossdressing for the first time

Crossdressing for the first time can be a daunting affair. Most men will find that they initially are drawn to a particular item of clothing, this would obviously be a natural place to begin. By starting small like this you will not only save money, but also work on overcoming your initial fears.

I don’t recommend it, but if you’d like to try getting dressed fully as a woman, you want to find something that will make it easy to look feminine. A skirt that ends below your knees and a long sleeve blouse is a good place to start. You may find that if you’re broad shouldered you’ll need to get a larger blouse than skirt. It is usually more difficult to find a dress that fits a man’s physique well. This outfit will hide your (likely) unfeminine knees, and broad larger biceps.

Make sure you shave your legs, arms and face. Put on a pair of pantyhose and find some low heels or boots to match your outfit. As for intimates, wear a bra stuffed with padding and a pair of panties to keep your unfeminine parts in check.

For clothes I highly recommend Newport News – I’ve found their size guides to be fairly accurate. They accept returns and have a good selection of clothes. For shoes Zappos has a selection of larger shoes (you’re likely to find you’ll need a wide, and a size or two larger than your regular shoe size).

Makeup is a bit trickier. If you want to be discrete you can order online, but it’s hard to match your color. As a general rule try to wear foundation that matches your skin color, or is slightly darker. Also, don’t go overboard on the mascara and lipstick – your makeup should accent your beautiful face, not be the first thing someone notices about you.

Good luck!

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About the Author

Vanessa Law is a women enjoying the freedom to be who she is every moment of her life! She blogs about the transgender journey at Please comment below and tell me what you think!

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  1. Taylor says:

    What could i wear as a 14 year old transwomen?? i’m just now starting to cross dress and starting to become intuitive.

    • Ragina says:

      hi Taylor, my name is Ragina. First off, welcome. You are fortunate first to know at such an age what you want. Second , that you have found this site. This is by far the best web site for girls like us. As far as what to wear for your first time dressing up, a little homework is in order( I know ” not more homework”). Study the girls around you and learn what they are wearing. At 14, most girls your age are already rather well on the way to a nice bustline(breasts), so a bra is definatly in order. I suggest using old pantyhose to stuff the cups, not too much, just enough to give you a nice appearance. Panties, of course are a necessity, so make sure you have some. The nylon type are very nice if you like something soft and feminine, if not then try cotton. I personaly recomend high rise bikini cut panties, but there again, experiment and learn what you like. Then, you can pretty much take it from there. If you chose to wear a skirt, then pantyhose are a must. Be sure to get the size that fits you. Look on the back of the package, there is a sizing chart there. Use it. Make up is an option as well. Don’t just get what strikes your fancy, but learn what type of skin tone you are and purchace make up that compliments that tone. From there you can get tips and techniques right here on this site. Don’t get disappointed at your first couple of tries at make up. It takes a lot of practice to get good at it. And most of all, my personal prayer for you is that you learn to love who you are. That is the most important advice that any one of us will give you. Good luck to you and keep us all posted as to your progress.

  2. Desere1 says:

    Victoria Stone : I shaved to look feminine ,my wife never got bent out of shape about it ,not even when I had shaved it heart shaped ! Your wife is going to find out about it ,why not let her know,she might want to be the one to shave you ! Joanna ,I wear a male 10 and in womens size that would be a 12 !I love my heels,the higher ,the better !

  3. Ryan H. says:

    Agreed about the shoulders problem. I would like to wear little springtime outfits with shoulders exposed but I find those really make me look somehow even more broad chested than normal so I go with blouses

    • Vanessa Law says:

      Ryan, I find the same thing. It’s frustrating, but then even genetic girls need to dress for the bodies they have. Besides, there’s lots of cute blouses out there :)

    • Terri says:

      i am afraid to go out as a cross-dresser, but with the right person I would do it is there anyone that could help?

      • Tracey says:

        I don’t know where you are located but if you are in northern illinois you are in luck. We have a meetup group that meets once a month. Total privacy and no reason to be scared. If you are interested please go to and look for northwest suburban crossdressing group. If you are not from Illinois there may be a crossdressing group in your area. It’s worth checking into.
        Good luck,

  4. Joanna McPherson says:

    I do have a major issue when it comes to buying shoes; I wear mans 12’s so Im never sure what size to even start looking at. The other issue is that I can’t even find shoes that big in my area.

  5. I like dressing up like a girl when i was 10 years old the first thing i put on was the dress they were my mother’s clothes of course i look more girly pretty too that’s all i ever wanted is to wear a dress panthose, and heels.

  6. Victoria Stone says:

    You gave me alot of help, but my biggest problem is with my penis & chest hair. I can not shave it because my wife will find out that I crossdress.

  7. Vanessa says:

    Thanks Lynn, I’ll take a look – it’s definitely a lot easier than fumbling through it yourself, though perhaps less fun than getting your loved one to share the secrets with you :)

  8. Lynn Jones says:

    A good selection of tips there!

    Finding advice on how to put your make-up on isn’t always easy. Luckily for us, sites like have online videos (all free, no registration required) in their Beauty Section.

  9. I wished, and wish that i’m more feminine even when i was a kid own dresses, skirts, bra’s, and blouses too.

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