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!

The following two tabs change content below.
Profile photo of Vanessa Law
Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.
  1. Patty Phose 8 months 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.

  2. Jada 2 years ago

    Yes! Finally something about tv media coaching.

  3. Thank you, I’ve just been searching for information about this subject for a while and yours is the best I’ve came upon so far.
    But, what concerning the conclusion? Are you certain in regards to the supply?

  4. http://saolmail.com/ 2 years ago

    Spot on with this write-up, I truly think this amazing site needs a
    lot more attention. I’ll probably be back again to see more, thanks for the advice!

  5. saolmail.com 2 years ago

    Magnificent beat ! I wish to apprentice while you amend your web site, how could i subscribe
    for a blog web site? The account aided me a acceptable deal.
    I had been tiny bit acquainted of this your broadcast provided
    bright clear concept

  6. Great post. I am facing some of these issues as well.

  7. My brother suggested I might like this website.
    He was entirely right. This post truly made my day.

    You cann’t imagine just how much time I had spent for this info! Thanks!

  8. You have made some really good points there. I checked on the net for more
    information about the issue and found most people
    will go along with your views on this site.

  9. islandia 2 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!

  10. Islandia 2 years ago

    Hello there! Do you use Twitter? I’d like to follow you if that would be okay. I’m definitely enjoying your blog and look
    forward to new updates.

  11. Frederick 2 years ago

    I just couldn’t leave your website before suggesting that I really enjoyed the standard info an individual supply in your visitors? Is gonna be back incessantly in order to inspect new posts

  12. ginger morgan 4 years ago

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

Leave a reply

Your email address will not be published. Required fields are marked *


©2015 Crossdresser Heaven | Privacy Terms of Use | Contact Vanessa | Advertise with Crossdresser Heaven

Chat is back up!Get your chat on

Discover Your Woman Inside
join the 6,200 woman of Crossdresser Heaven

Join the Crossdresser Heaven Newsletter and get tips and encouragement


Log in with your credentials


Forgot your details?