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.
Loading ...
Vanessa is a happily married 30 year old transgendered woman from Seattle. It's been a long road to acceptance for her, despite the fact that she has been crossdressing for more than 25 years. Sometimes, when she looks in the mirror she longs to see the girl that lives
within her. 
23 Comments
> 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
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
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
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
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
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
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.
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?
Kelly, thanks for the great tips! I might repost these as an article so other folks can see them as well. Very valuable!
Thanks for the fine advice. Sofisticated, well explained and useful.
I can´t wait to go in public but have no company. Love to look younger than 60, but…
I can´t pierce my ears either and love big earrings.
First time at your website. I´ts fantastic
Thanks. Keep it up.
Hey Priscilla, thanks for stopping by, I’m glad you found the website valuable. There are many great clubs all over the country that cater to crossdressers of all ages. I’m staring down at 30 (less than a month to go!), so I guess I can empathize somewhat. I’d love to be 14 and discovering who I was. there are probably things I would have done differently. But I’ve had a blessed journey as who I am, even if I’ve got more wrinkles than I’d like
Hope to see you back soon.
Hugs,
Vanessa
Do you have any tips for a guy thats 31 years young 6ft 4in weighs 225lbs and has a lot of tatoos. I embrace my manly side as well as my fem side. I already have my style down for my manly side. Now I gotta find a style that best suits me for my fem side. I like the Amy Winehouse look. What do you fabulous people think? Someone please help!
You got that one wrong.
For one thing, like someone mentioned previously, some of us don’t dress to pass, just because we like the clothes. Nevertheless, when I pictured myself as a woman, I was wearing a bridesmaid gown, bridal gown, or prom dress, or a knee length pleated skirt with modest heels (just a couple of inches), and a pretty blouse — and no stubble, pretty hair, etc.
Don’t get me wrong, I like your blog, thanks. If anyone out there wants to read my blog, I wouldn’t mind a visitor or two either, LOL.
MaidMichelle.blogspot.com
Some more tips would be great. Any more information and experiences are appreciated.
Greetings to all I’m new to CDH and have read with joy all that I can. I have CD most of my life but tge demands of family and society it was always in private.but now that I’m 56 yrs.old and those demands are mostly gone I desire to become who I have always been on the outside.within has always been there.so can any one please help me with age appropriet tips on fashion and makeup.thanx all. Leona
Welcome Leona, it’s great that you could join us at Crossdresser Heaven! The best place to start is to watch woman your age. See what they wear. Look at woman who are roughly the same build as you and see what suites them. Some tips apply to woman of any age (such as sunscreen!), check back here often for makeup tips.
Greetings to all.you have said to watch woman my age and style.I do and have learned so much.rihgt now for me the gresatest joy is allowing my dominate fem side to take from my male side those things that can make me undrestanding of who Leona is.slow prosess but one worth the wait.untill next time.Peace to all
hi. i am sorta new to cd. i have always been a closet cd and have never done it in public. i do have very hairy arms and legs (which i cant shave, because i deal with to many people at work). i have finally worked up the nerve to do it in public, what do u suggest to cover up my arms and legs (noting that it is summer and hot out). thank you~lisa
Phew, you’re in a bit of a bind there hon. In winter there are all sorts of tricks to use (stockings for the legs, long tops for the arms). There are many men who don’t have very much leg or arm hair, and I’m willing to bet many men at your workplace won’t even notice if you didn’t have arm hair. Even more so if you removed the hair gradually. Either way, you need to commit. Don’t let your hair grow half out after shaving – people are more likely to notice this.
Hugs,
Vanessa
Hi all. I am relatively new to this, but I have a suggestion for anyone who wants to be able to shave their arms, but like LiSa feels that people will notice the change.
You could claim to be getting heavily into cycling- cyclists shave for safety reasons. If they fall at speed the hair would otherwise melt with the friction, and remove large patches of skin. It leaves very large scars, so they avoid this by shaving arms and legs. Whether you actually get around to riding is irrelevant.
Also I have started keeping an eye on women who have broad shoulders, like swimmers, to see what outfits I could get away with wearing.
I love to dress the way the young actresses and models dress,very stylish and sexy outfits and i love the dark makeup,although as i get older i’m getting better with it so i do tone it down a little.I know i would stand out like a sore thumb if i wore this in a shopping centre on a wet Tuesday afternoon,especially with my 5inch high heels on,but as i never leave the house dressed or want to,i’m so happy as i am.My wife is ok with my dressing as long as it dosen’t rule my life,so over the years i’ve settled into a pattern of just once a week,she calls it my little hobby,but she shops with me for my makeup and clothes.
Hugs
Nikki
Nikki, it seems like you’ve settled into a good routine with your wife. I’m happy for you. It’s sometimes hard to find the right balance in a relationship between what the crossdresser wants and what the wife wants.
I started to crossdressing when i was 12 yrs. (now I’m 42) with my sister’s bra and panty. Now i buy my own woman’s clothing including Bra, panties, wig, cosmetics and shoes too. But im a secret CD never done in public. Every night I have been dressing in female clothes and sleep with it, for years and the feeling is fantastic. Now im very desire to going out but no company and shy. Im never been friends to other CD’s. I’m planning to A holiday to abroad, and going out to public as a woman, what sould i do. I need help.