The first time a man puts on a dress he looks like - a man in a dress. In our minds we picture ourselves as dainty, feminine and gorgeous, but we’re actually a man caught wearing girl’s clothes. Looking good as a woman is a hard thing to do - just ask any lady who has spent an hour doing her hair and makeup!
If you’re just looking for some quick tips on what to wear the first time you cross dress then my previous article is the right place for you to start. If you want to look fabulous, and pass as a genetic woman - then read on!
There are seven aspects to looking great and passing as a genetic woman every time:
- Wearing clothes that make you look good
- Making sure your curves are in the right places
- Feminine body movement
- Hairstyle that feminizes your face
- Natural makeup
- A feminine voice
- Loving who you are as a woman
Do we want to look like men wearing dresses?
NO! If you’re like me, the image you hold of yourself is as a beautiful movie star, not a guy in drag. The truth is that we can all look and feel beautiful - but it takes some work. Over the next few weeks I’m going to share with you some of the secrets to looking like the woman you see inside - to cross dress for success.
If you’re eager to look fabulous today, I highly recommend the World’s Best Cross Dressing Guide. You’ll get all the tips and tricks you need to be the woman you are, and complete your male to female transformation!
Before we get started though, I want to share with you the biggest mistake men make when they wear woman’s clothes. This is probably the number one reason why cross dressers fail to pass, and end up looking like a guy in drag instead of a passable woman.
Before I share it with you, think for a moment on how you picture yourself as a woman. Let me guess, high heels, short skirt, dramatic makeup and plunging neck line. Am I right?
The biggest mistake the transgendered make is that:
When men cross dress they try to look like a whore
Not many woman would be caught dead wearing 6″ heels and a mini-skirt that barely covers their panties. Yet cross dressers try to dress like this - they’re dressing as their own fantasy girl. Take a tip from genetic woman - most of the time they are dressing for their girl friend, or to impress other woman. They are trying to out do other woman, not fulfill a man’s sexual fantasy.
Even if you’re lucky enough to have all the other attributes of a woman, if you dress like a whore you will stand out.
In the first lesson (coming next week), I will teach you how to wear clothes that make you look good, so you can cross dress with confidence.
Tags: Crossdresser How To, crossdressing, how to crossdress, learn to crossdress
March 26th, 2008 at 1:51 pm
> Am I right?
One out of four isn’t bad.
You got me on the heels, but my feet look like boats in flatties. While I may wear heels, they’re not that high - not those “FMSs” that people keep for the bedroom.
For what it’s worth, I think you can do a lot worse that taking note of women your age are wearing….
Note, this won’t work if a) you live on a filmset or b) hang out near a strip joint. Those looks are for the professionals only
April 11th, 2008 at 5:26 pm
You wrote, “think for a moment on how you picture yourself as a woman” but….
I think you’re forgetting that for some people “cross dressing” just means wearing clothes typically associated with the gender opposite to their own. I don’t dress to pass as a woman, I dress because I enjoy wearing women’s clothes. There’s a big difference between dressing in women’s clothes and trying to look like a woman. But they can both be considered ‘cross dressing’.
You seem to also be overlooking women crossdressing in men’s clothing. One of my partners does that sometimes, but she does it for a more theatrical effect, not a fetish and not to pass as a man.
It’s too bad that your outlook on crossdressing is so narrowly focused. You seem to have some good advice, but you seem to be assuming that everyone is just like you. And though I don’t know much about this big ‘ol world, I do know that we’re not all alike.
Kind regards,
A
April 17th, 2008 at 8:38 am
It’s a funny world we live in when you think of it. I am surrounded by very badly dressed WOMEN every single day. I am thinking that you chaps should be giving them tips
If you see those programs (in the UK) called ‘what to wear and what not wear’ you’ll get an idea!
I suppose therefore who you emulate is very important. Emulating the women out and about might actually NOT be a great idea.
Perhaps find a role model celeb who might match you in build ……….ok forget that, these days those women don’t even look like real women!
Who to model yourself on?
Somehow somewhere you need to find a female that matches your build, one with good taste in clothes and try to learn her secret.
I am thinking these resources might be helpful:
Catalogs for
plus size women
tall women
petite women
might actually be fairly helpful?
Meanwhile here’s an important tip ( I shall use this tip on my blog if you don’t mind Vanessa!!)
If you are tall and you wear a short skirt with panty hose (tights) they tend to creep down at the gusset and so when seated or even standing the pantyhose come down lower at the crotch than the skirt!! This is not attractive on either sex!
So my advice
Keep those skirts nearer the knee than the crotch to avoid this ‘crotch hang’ effect.
Leah x
November 28th, 2008 at 11:22 am
Hi
I have been dressing in female clothes for years and the feeling is fantastic, a nice little black dress, tights, panties, bra, and heels, it is just a pity my wife does not like agree and join in my fun, woman are so lucky in the way they can dress, us men are so bloody drab, I am new to your site and it looks very helpfull will be back.
Love Wendy
November 29th, 2008 at 5:00 pm
Hi Wendy, thanks for writing. It’s tough when those we love don’t accept this part of us, but I’m happy that you’ve taken some time to express yourself as well. Without this I think we die a slow death inside.
Hugs,
Vanessa
November 29th, 2008 at 11:06 pm
You asked for tips on passing as a woman:
1. Dress your age. If you aren’t a junior, don’t buy your clothing in the juniors department.
2. Dress appropriately for the situation. A cocktail dress at the mall isn’t optimum. Make up needs to be appropriate.
3. Crossdressing is an illusion. A genetic woman can go out without any make up and can look a mess but not look like a man. You can do the same as a man and not look like a woman. You need to constantly preserve the illusion and this involves diverting attention away from your flaws and using clothing and most importantly accessories to preserve the illusion. I do not need glasses but found they feminize me so I bought some (in the women’s section of an eyeglass store). wearing men’s glasses simply is not good enough in 99% of the people I know. I wear a hair band, diamond engagement ring, chain bracelet, necklace, earrings that dangle, and red lipstick because many people have critiqued me and said these things feminize me. The red lipstick and nail polish divert the eyes away from other parts of me.
4. Choose a wig wisely, This may be among the most important things you do. Length, color, style all matter. (If it is too perfect, it will look fake.)
5. Hair removal is always an issue. You think nothing of spending a great deal of money on clothing and cosmetics so spend some on a quality razor. Consider hair removal on your face if necessary. I had laser hair removal and it was the best thing I ever did. Use the right foundation to cover the beard but shave it off first! covering is not as good as removing. Shave closely and several times.
6. Apply make up skillfully.
7. Cover your arms if you need to. My arms are larger than a woman’s so I wear some type of top. This means I never get to wear sexy cocktail gowns and expect to pass but I can usually find something nice with sleeves. Cover your Navy tatoo!
8. Keep your skirt length appropriate. In fact, keep everything appropriate. Anything that looks out of the ordinary will be noticed and once you are noticed you will not pass. Much of the time if others really noticed me i would not pass yet somehow I pass extremely well. Why? Because I blend in and fly under their radar.
9. Avoid direct confrontation with anyone and when it i necessary to interface with a waiter, store clerk, etc. be prepared. When i go to the grocery store i know they will inevitably ask me paper or plastic so I am ready and reach for a plastic bag. I know I will be asked cash or credit so I have my cash or credit card in my hand where they can see it before they ask. But if I have to speak, I speak softly and quietly and smile.In a restaurant, point to the menu item as you order. This reduces the need to fully speak in detail.
10. Choose where you go in public carefully to minimize problems. If you don’t really pass, stay out of the ladies’ room. I go out at any time of the day or night in Times Square and pass but I avoid groups of teenagers like the plague. They will notice and if they notice they will not notice quietly.
11. Walk like a woman not a caveman.
12. Relax. If you are afraid, you will walk like you are afraid. Have confidence.
13. I’ve seen many men who do not prepare themselves to pass. One CD friends is an auto mechanic and he shows up at support group meetings with black grease on his hands.
14. Eat and drink like a lady. I love beer but more women drink wine so i drink wine. Men stuff their faces. Women are much more, well, feminine in how they eat. Study female behavior so you can emulate it properly. A word about smoking. I personally feel that smoking is one of the easiest means to tell if someone is a CD or a real woman. Few men can smoke like a woman. You think you can, but you can’t.
15. Carry a mirror and use it. Men don’t need much attention but women need constant attention. Walking from the parking lot to the Mall can result in blown hair. Eating can alter make up. Be prepared.
16. Smell like a woman.
17. Pay attention to detail. You may not be into make up and real women don’t need it to look like a woman but it will really help you. Curl your lashes. (No, don’t use artificial lashes). Keep your clothing stylish. No, that man’s coat isn’t going to pass as a woman’s coat. Details! If you have a huge Adam’s Apple, wear turtle necks. Learn to adapt.
18. We all want to have our own set of 52 DD tits but if you wear 52DD tits you are going to attract attention and you will therefore be noticed.
19. Be self aware. Know your limitations. Unless you have practiced dancing like a girl you probably won’t do it like a girl.
I hope these will help you.
Kelly Stevens
December 27th, 2008 at 3:21 am
i crossdress to just fit in with my family as both my mums and my three sisters think i should have been a women and have always dressed me in girls clothes, and called me sophie.
December 28th, 2008 at 4:19 pm
Hey Sophie, thanks for stopping by - welcome. That’s an interesting way to start crossdressing, one I’ve rarely heard. Do you know why your mom and sisters thought you should’ve been a woman? Do you resent this, or has it been a blessing in your life so far?
December 28th, 2008 at 4:40 pm
Kelly, thanks for the great tips! I might repost these as an article so other folks can see them as well. Very valuable!