What to wear the first time you crossdress

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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  1. Lynn Jones 9 years ago

    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 videojug.com have online videos (all free, no registration required) in their Beauty Section.

  2. Vanessa 9 years ago

    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 🙂

  3. Victoria Stone 9 years ago

    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.

  4. Josephine Shaffer 8 years ago

    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.

  5. Joanna McPherson 8 years ago

    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.

    • Profile photo of Vanessa Law
      Vanessa Law 8 years ago

      The Internet is your friend 🙂 Zappos and Amazon both have good collections of larger shoes. Amazon had a pretty good sale on a while back. I’m not sure if it’s still going. I’d start with a size 13 wide (D). Though if you’ve got larger feet you might also want to try E or 2E

  6. Ryan H. 8 years ago

    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

    • Terri 8 years ago

      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 7 years ago

        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 http://www.meetup.com 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,

    • Profile photo of Vanessa Law
      Vanessa Law 8 years ago

      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 🙂

  7. Desere1 8 years ago

    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 !

  8. Taylor 7 years ago

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

    • Ragina 7 years ago

      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.

  9. jennifer 7 years ago

    The mistake crossdressers do when they first go out is they dress to much and too much makeup. Dress like a classy woman with pantyhose a skirt and a nice top and do your hair normally with a few bangs and never overdo with makeup. Just a little touch with blush,eveliner and eye shadow and lipstick and you will blend in with the crowd.

    • Profile photo of Vanessa Law
      Vanessa Law 7 years ago

      A mantra of mine – never overdo makeup. I guess it’s still an overreaction from seeing early photos of myself – sheesh! You’d think I’d dipped myself in the blush container 😉

  10. leona 7 years ago

    Hello Taylor my name is Leona. Ragina and Jennifer gave such great advice. A nd this site will be of great help. We all want to look beautifull and we sometimes go to extreme on make-up and things. I have been guilty of this more than once. So dress your age and the most important. Be yourself. You will find that your confidence will grow as you do.

  11. Terri 7 years ago

    I have no idea of just how to or what to wear if I ever go out of my house cross-dressed, for I have no help with me. I cannot get any help with just how I should look as a ladied, and no one will even tell me where I can get any help.
    how can any one help me or where is the help?

    • Ragina 7 years ago

      Hi Terri, I’m Ragina. I’ve found that the easiest way to Find out what to wear is just to watch other women and learn what they wear and then pick out your own wardrobe accordingly. There is so much good advice here on this site. Pick out a subject and study it , then spend some time and practice, such as make up. I used up so much make up learning to do mine right you wouldn’t believe. Of course, if you have a wife, girlfriend,SO, or other female friend that you trust, you’ve got one of the best teachers going. Use the resources that you have, and enjoy being the woman you were meant to be. Love ya. Ragina

  12. Tracey 7 years ago

    I am a straight female who has an amazing gurl friend. Through her I have learned so much. This is what I have found confidence is more important then the clothes. Don’t wear 3″ heels is you can’t walk on them. I see so many women doing that and it drives me nuts. Wear something you are comfortable in. Most women can tell the difference between girls and gurls. Honestly we don’t care. Actually most of us are jealous. You look better in our clothes then we do. Just relax and enjoy yourself.

    • Profile photo of Vanessa Law
      Vanessa Law 7 years ago

      Thanks for stopping by Tracey and for sharing some wonderful advice. I’m amazed at easily I’m read when I’m nervous about being read… and how noone seems to care when I confidently step forward smiling.

      • Tracey 7 years ago

        Vanessa you are amazing. You don’t have anything to worry about.
        Happy Holidays Love,

  13. Carol 7 years ago

    The first time I went out, as Carol, I remember it well. I had a brown page style hairdoo, I wore a blouse and sweater, a black skirt and a pair of penny loafers. Plain suntan hose. I swung my purse over my shoulder and off went, and 30 years later Im still alive and enjoying every time Im out.. as ME!

  14. Jen 7 years ago

    It is my first time cross dressing. Actually been trying for a while, back about 12 years ago I went to a store trying on dresses. They where very good with me and I had to makeup test person do my face. Yes a lot of people looked at me weird.

    So I am starting with bras and I am having a nightmare. I am a bit heavy and very heavy for a lady. Close to 300 lbs. So I have natural breasts, which I am more excited about then embarrassed about.

    My ex girlfriend was about the same size as I am, so I kind of knew around what bra size I should try. So I bought a 44B. It was a bit tight on me, but I am not sure how tight bra’s should be, as a “normal” guy I am used to wearing lose clothing and quickly learning that women clothing is not lose.

    How tight should the bra be? I have been reading a lot about how it should fit and how to find the messurments. If I go by what I ready I would be a 48D. However my breasts seemed to be to small for the 44b I bought. In one article I read it said if the cup wrinkles then it is to big, try a size down. On the 44b the cup wrinkles a little, which by what I have read I would need a 44a….the big kicker is that I can not find a 44a. I am not sure if the even make that size?

    They have a ton of 38 – 40a’s. Should I buy the 38 and maybe buy an extender so I can close it in the back?

    Next quest is about the skirt. I have NO CLUE what size to buy – Hip is 55, Waist is 50. Do I wear the skirt on my Hip or Waist? Naturely I wear my jeans around my waist.

    Once I get this all set it will be so much fun, I think God intended for me to be a female, I have a female voice, long finger and long eye lashes and I am able to grow my finger nails out really nice and long with no effort 🙂

  15. aeros46@hotmaIL.COM 7 years ago

    all i want to knwo is how ot crossdress in my own home as i;m disabled and all the meds i;pm om give me hoit flashes i just want t be comforgtable and i kniow enms clothes r too thick need just some advice

  16. Michael 7 years ago

    I am just about to go in public as "Michelle" Full make up, skinny jeans, cami, sweater and wig. I don't want to brag, but holy s@#$t I look hot!

  17. ginger morgan 6 years ago

    ihave 3 days till i go on my date i need help looking foward to talk to you ginger

  18. islandia 4 years ago

    I’m really enjoying the design and layout of your site. It’s
    a very easy on the eyes which makes it much more enjoyable for me to come here and visit more often.
    Did you hire out a designer to create your theme?
    Outstanding work!

  19. Jada 4 years ago

    Yes! Finally something about tv media coaching.

  20. Patty Phose 2 years ago

    I usually avoid sleeveless dresses. If I really like a sleeveless dress, I’ll wear it with a matching or open longer sleeve blouse. My legs are always hair free and I always wear pantyhose when showing them. I do have a passion for short dresses and skirts though. Above the knee is good. Mid thigh is better.

  21. Atef Anwar 1 year ago

    This is a first time to wear a crossderssing. I prefer to wear high fitted neck or peter pan collar dresses with back button because my neck is thin and tall. I wear also a fitted bra and still in home alone and l am could not go outside.please what can I do?

  22. Profile photo of Patty Phose
    Patty Phose 11 months ago

    The first time I dressed fully fem, putting on pantyhose was no problem I had been wearing them for years. I wore heels because I liked how they made my legs look better. They did take some getting used to though. Makeup I needed a lot of help with. The dress was very comfortable. Padded bra, no issues there. A few different wigs and I decided on the long blonde one. Panties were worn over my sheer to waist pantyhose.

    I thought I looked terrible but I got a lot of compliments. It was a Halloween party and I was 18 so I probably got a lot of latitude.

  23. Lovely1117 6 months ago

    Just be you no matter what people say

  24. ginger morgan 6 years ago

    i am a crosserdresser who is going out on a date for the time with a man ihave never kissed a man or had sex witha man what do i expect and what should i do please help ginger

  25. Josephine Shaffer 8 years ago

    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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