What to wear the first time you crossdress

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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Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.
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  1. Lovely1117 3 months ago

    Just be you no matter what people say

  2. Profile photo of Patty Phose
    Patty Phose 8 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.

  3. Atef Anwar 9 months 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?


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