What to wear the first time you crossdress

Crossdressing for the first time

Crossdressing for the first time

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!

Tags: , , ,

About the Author

Vanessa Law is a women enjoying the freedom to be who she is every moment of her life!

49 Enlightened Replies

Trackback  •  Comments RSS

Sites That Link to this Post

  1. mediator craiova | October 12, 2014
  2. facebook likes appear in news feed | October 5, 2014
  3. thingsmewant.com | September 19, 2014
  4. Ruby's Tips for Crossdressers | Ruby'sRuby's | May 8, 2013
  5. Learn how to cross dress | Crossdresser Heaven | April 22, 2012
  1. Patty Phose says:

    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 says:

    Yes! Finally something about tv media coaching.

Leave a Reply