Here is a Blast from the past from our site owner, Vanessa. Published originally on March 3, 2008
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 Lucille’s Stepping Out Secrets. You’ll get all the tips and tricks you need to be the woman you are, and complete your male to female transformation! I used Lucille’s resources when I completed my transition many years ago, and she is the real thing!
Learn How to Crossdress and Step Out
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.
More Articles by Vanessa Law
- Win a Free Makeup Prize Bundle from Jecca Blac
- A Few Changes in Our Family
- I Want to Live Like That
- Hope in Despair, Light through the Darkness
- Scholar Program – Transwomen’s Social Support for Medication Adherence
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… Read more »
Trust me, no one cares. Don't ask, don't tell. If anyone (usually 'best friend') asks, just tell him you like it this way (or wanted to see how it goes).
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… Read more »
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.
How did you get to the point that u were confident in looking enough like a woman that u could go out in the day time and still be able to meet peoples eyes and smile as u walk a busy street and deal with all the eyes u know are on you or think are on you? What do you do for work now? Have you grown breasts or had implants? Are you pre-op? I know I do want the reassignment surgery but in time. I dontw ant to get implants id rather grow them but im worried about… Read more »
Hi! As far as the confidence issue goes, that wasn’t much of a problem as I’m rather outgoing to begin with. The looks came courtesy of my wonderful wife. From the time that she accepted me she has made it her job to see that I know what I’m doing so that I look acceptable. Now for me personally. I’m 55 yo, and retired on disability. I am married for 20 years and have 5 children, the youngest is 8 yo. I spent 22 years in the military, including a tour in Iraq. As far as your questions, the answer… Read more »
so i told my parents today and my step sisters my dad is heart broken cause i felt i couldnt go to him about as I was afraid to tell him that he would pop a vein. My step mom is very supportive i hugged her twice tonight and told her i loved her and she loved me she had to fight back the tears each time. My step sisters are so supportive its amazing despite how distant we have been for so many years and todl my step mom hey like we have to support him and my step… Read more »
The heading of the reason crossdressers dressing to look like a whore, isnt accurate I think anyway. These are fetishists and bizarros who are in a sexual existantial fantasy land. No decent woman would dress like that, and neither would any crossdresser with any scruples. You ARE what you look like. Dont give the rest of the community a bad reputation. You can leave by the back door….. just slide under it on the way out. You get the picture.
Justin, I’m so happy that you now have the support that you need to begin your transformation. Hang in there, I’m sure that your Dad will come around if you talk to him in a positive way. It’s a real shock to a father when a son has to make such a drastic change in his life such as what you are doing. I don’t have any suggestions as to what to say to your Dad to help him understand why you are doing this, so unless someone else out there can give you some advice… Otherwize, My prayers are… Read more »
Hi Lakshmi, The best place to start is to learn a bit more about what you’re feeling, and to find resources either online or at a local library. The books I’ve linked to on Crossdresser Heaven are a great place to start, there are also many other blogs from teenage crossdressers who may give you a more insightful look from their perspective.
I recommend starting with this article: https://www.crossdresserheaven.com/a-teenage-crossdresser/
im a college going student i cant express my fem side since i dont have any sisters to try their clothes. i have bought only a bra and panty with my pocket money …. im so upset by this and what shall i do. . .
go to Goodwill store (try anything you find right there, the personal are friendly to all CDs), or go to Salvation Army store. Used is as good as new, but way cheaper! For boobs, just buy nylons, cut them off, put bird seed (or rice, but classic advice is bird seed) into it, and then make a big knot (that's your nippie!). Try it on, if there's to much, remove some. Don't overdo it! Go for B or C size (choose B). Measure you breast with the bra on and waist, go to JCPenney or Target and see their fit… Read more »
Does anyone have any tips on crossdressing – for a woman? That is to say, passing as a man?
Hexiva. Having known a number of TS female to male types, Id say just dress like the guys do, jeans, and a loose t shirt, to cover your hips if you can get away with it. Cut your nails short. Wear short hair, dont over do it, but if you do get read, nobody cares, as there a lot of girls that cannot pass for their own gender, save their voice!
Having re read my post above about why crossdressers look like whores, is what I feel to be essentially true. Those of us who are living the hellish existance of a TS night find the slutty exhibitionists offensive. I wouldnt wish being a TS on my worst enemy. Life is tough enough without having to watch the circus of whores come to town. Now lets get on with it.
Hi Van: I did not put that paragraph in perspective. I was referring to the statement on the site asking why SOME crossdressers want to look like whores. I was out of line if you or anyone else thought I had all crossdressers dumped into that lewd catagory. With the road of a TS being a hard road, your dam sure it is. hasent it been for you? I wouldnt wish such a thing on anyone. I missed the potential of my youth when I couldnt live in my true gender. That was unhappy, along with other defeats, that go… Read more »
Yikes, that’s quite a story – it’s hard to believe that things like that would go on. No worries love, we all say things which can be interpreted differently by others.
I’m just at the beginning of my ts road. You could say I’m still packing the car for the trip, so I don’t think my perspective is… rich enough yet to comment with authority about the road to womanhood.
Hugs,
Vanessa
Carol,
I don’t think your characterization of crossdressers is fair or warranted. It’s true that many crossdressers dress inappropriately – perhaps fueled by a mistaken male perception of what makes a woman look good. However we are all on our own journey, and would do well not to judge others too harshly.
I’m sorry that your experience of being transsexual is difficult. For many it is a hard road.
Perhaps by being more accepting of others you’ll find that others are more accepting of you.
If you read my comments they reflect upon crossdressers who look like whores. NOT all crossdressers, as the fetishists and deviates are the culprits. Not all crossdressers. Not all crossdressers, is that clear?!!! I was screener for several years of a crossdressing support group back years ago. It was my job to direct peoples inquire, and weed out undesireables from our meetings. I thought I did a pretty good job, until I noticed some members dressed like trash, wearing provotive attire, obvious fetishists, who didnt hide the fact in their actions or in their subject of conversation. We had comments… Read more »
how to walk talk act sit stand like a teenage girl…???