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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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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Atef Anwar
Atef Anwar
7 years 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?

Patty Phose
Famed Member
7 years 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… Read more »

7 years ago

Just be you no matter what people say

Casey Case
6 years ago

So much makes so much sense when I read it, just wouldn’t have thought of it on my own. After about a year of dressing up at home I feel I have moved into a different mindset. Not just putting on women’s clothes, but just like you wrote, wanting to look more feminine. I get how that feeling changed and guess it was inevitable looking over the last few months. I bought makeup for the first time yesterday. Application is much harder than I expected, at least I was able to laugh about it, the results were pretty hysterical, okay… Read more »

Staci Gal
Active Member
1 year ago

OK, I am new at this – sort of. I am a crossdresser in the sense that I have been wearing gals shoes (flats and heels), but as a guy, since I was a teen. The first time I crossdressed, I was about 10 years old and “for fun" my grandmother dressed me and my brother up as girls. We all laughed and joked, but actually I kinda liked it and the memory stayed with me. When I went away to college, wearing gals shoes became an almost full time thing. Got married, the wife was aware of my gal… Read more »

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