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.
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hello,
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?
Terri
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… Read more »
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.
Tracey
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.
Vanessa you are amazing. You don’t have anything to worry about.
Happy Holidays Love,
Tracey
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!
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… Read more »
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
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!
🙂 I love your confidence hon! Good luck!
ihave 3 days till i go on my date i need help looking foward to talk to you ginger
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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.