Category Archives: Learn How To Crossdress

2 Crossdressing Mistakes We All Make

By Vanessa Law | Published August 28, 2010 | 5 Comments |
Two Crossdressing Mistakes

Two Crossdressing Mistakes We All Make

I gazed around the room. Every lady was well put together – to an individual her outfit was coordinated and appropriate to her build. Her makeup was subtly and carefully applied. Her hair styled with the love of a salon owner. These ladies had clearly learned how to crossdress, they had avoided the most common crossdressing mistakes and then some.

Yet as I looked at many of these lovely ladies I couldn’t help thinking “man in a dress”. That thought stunned me – these women could all be role models in the crossdressing community. They had cultivated their appearance and would be the envy of any just beginning their crossdressing journey. It also made me pensive – if that thought so quickly entered my mind, and I admired their appearance so, surely I’ll be read even more quickly? In fact, what hope is there for any of us to pass as a woman?

After mulling it over for a few days I finally figured it out – these ladies made 2 crossdressing mistakes. Mistakes we all make.

Crossdressing Deportment School?

Men are relaxed to the extreme. When they sit they spread out, taking as much space as they need to fully relax every body part. When they walk they take up space, and they slouch. Their shoulders stoop over as if finally bending to years carrying the heavy load of masculinity. Woman don’t slouch – woman sit and stand up straight. Watch woman next time you’re out shopping, and compare their posture with the men you see. If you can catch a multi-gendered checkout line the difference will be immediately obvious.

Now “stand up straight” might bring to mind a relative you know who is in the military. There’s nothing feminine about standing to attention as if preparing to salute the president. To get a more feminine posture you need to think “in and up”. Roll your shoulders back and gently drop them. Pull your elbows in and lift your torso up as if you’re  a puppet on a string, with the string coming through the crown of your head. Lean slightly forward and then soften your posture. To make good posture a part of your daily routine I highly recommend taking up yoga – many of the poses will help undo years of bad habits that gives us all the inevitable slumping forward.

The first mistake these lovely ladies made was to slouch.

Life’s Not That Bad, Is It?

It was clear all the ladies were deep in concentration – learning the latest tips on how to present in a more feminine manner. Their brows were furrowed, their lips pressed together in a contemplative frown, and their face pulled down as if they were wrestling with the information presented. It was also clear that this look was working against their desires to pass as a woman. For most men their face “at rest” is in a slight frown, yet most woman have a more radiant, open and uplifted face. This can prove quite a challenge for transgender woman, since most of the time we don’t think about what our face is doing until we express an emotion.

What can we do about our propensity to frown? Find something joyful in every moment, and let your joy show. That’s much more effective than plastering a fake smile on your face – and as a bonus you’ll feel better too :)

Do you want to avoid other crossdressing mistakes?

If you want to hone your feminine presentation I highly recommend you purchase the ultimate crossdressing guide. And practice practice practice! You’ve spent years hiding your true self, and it will take time to break through all the masculine walls you’ve built around yourself.

With love and blessings,
Vanessa

5 Comments | Also posted in Crossdresser How To | Tagged | Trackback URL.

Crossdressers In Pursuit of The Perfect Feminine Figure

By Vanessa Law | Published August 16, 2010 | 13 Comments |

Crossdresser Body ShaperIt’s happened to all of us. We finally pluck up the courage to purchase an outfit of our very own and spend many days or weeks admiring our new femininity in the privacy of our home. The feelings of elation seem to touch to the core of our soul as we see the woman inside us come to life. Yet after a few weeks something happens.

We observe that the dress doesn’t hang right. The sexy blouse seems to gape in an unattractive way. Even in the dim light of evening we struggle to describe our hourglass form as such. The elation of those first tentative steps are replaced with a low grade despondency a frustration at how far our form is from the perfect feminine figure.

Enter Crossdresser Body Shapers

With some guidance from fellow crossdressers, or a few keystroke search over the Internet we find the answer to our feminine figure frustrations – body shapers. The most obvious starting place is, of course, breast forms. Of all the things missing from our bodies breasts are the first and most obvious we notice. Breast forms do the obvious – creating the appearance of real breasts, especially when carefully concealed behind a blouse or dress that masks their artificial nature. There are many places to purchase breast forms – in fact you’ll find a link to the Breastform store at the bottom of this page – but your figure firm ups don’t need to stop there.

As you know woman tend to have larger hips and curvier bottom than men. The balance between larger hips and smaller shoulders gives woman the desirable hourglass figure. As long as you don’t make the mistake of wearing a top with shoulder pads or copious gathers around your shoulders you’ve done about all you can do for your shoulder size. Your bottom half, however, presents an opportunity to further your feminine image. Hip pads and bottom pads are body shapers that many crossdressers use to balance out their wider shoulders, and give the appearance of a curvier, hourglass figure.

To take the illusion to the next level you can wear a corset, which makes your waist smaller through the painful application of a smothering force around your torso. Oftentimes you can take 2-4 inches off your waistline with a corset. Just be careful not to tie it too tight – it’s no good looking fabulous if you’re passed out on the floor!

Vanessa’s Body Shaping Routine

I must admit that I’ve found over time that I prefer fewer enhancements than more. Perhaps it’s just my desire to feel comfortable, or maybe I’m just fleeing from the struggle to keep those breast forms attached and happy. When I’m out with jeans and a tshirt or blouse I’ve found the lack of breast forms doesn’t make much difference as to whether I’m read or not. I’ve had less success going breastformless with dresses, or certain blouses that hung uncomfortably empty without them.

I generally don’t use hip or butt shapers – though if done right they can look fabulous. I haven’t worn a corset for a few years – for now I’m focusing on slimming my waist through diet and exercise. Once I’ve taken that as far as I can I’ll give the corset another try.

What about you? What’s your crossdresser body shaping routine?


What figure enhancers do you use when crossdressing?

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13 Comments | Also posted in Crossdressing Polls, Fashion, Clothes and Shoes | Tagged | Trackback URL.

Finding The Perfect Pair of Woman’s Shoes

By Vanessa Law | Published August 8, 2010 | 6 Comments |

For the crossdresser taking their first tentative steps out in the world so many questions swirl around them. Will anyone notice me? What will they think? What if I meet someone I know? Among all the questions perhaps the most important goes unasked: “Do these shoes go with my outfit?”

Unfortunately for many crossdressers the answer is usually no. Many crossdressers don’t spend enough time enjoying the true diversity of woman’s shoes available. Most of us are just happy if we can find a pair of high heels we can squeeze our overly large feet into. The time we do spend looking for shoes is usually results in a shoe collection that would make a stripper blush.

Now don’t get me wrong I love stilettos as much as the next girl, but it’s difficult to enjoy a day at the park in on 4″ heels. Today I’m going to share with you a few tips for finding the perfectly fitting shoe, as well as some other fun shoe styles to try. If you know all this, and just want to find some great places to buy larger woman’s shoes you can find all the details on the crossdressing high heels page.

Crossdressers – Choose Your Woman’s Shoe Size Wisely

When selecting a woman’s shoe you should pay attention to the two measures of size – length and width. The first of which is the length, indicated by numbers (8, 9, 10, etc.). If there is no width specified it normally means the shoe has a Medium width, which get proportionally larger as the shoe size increase.

The second measurement is width, which you’ll find expressed by letters. AA for Narrow all the way to EE for the widest width.  Confusingly enough you’ll also see width expressed using a different set of letters: N, M, W and WW. They’re measuring the same thing, so a handy way to think about it is:

  • Narrow: N or A/AA
  • Medium: M or B
  • Wide:W or C/D [Equivalent to a Men's medium]
  • Extra Wide: WW or E/EE

To find your woman’s shoe size you need to add one size to your men’s dress shoe size (round up if you wear a half size), and take your men’s shoe size width and add one. So a men’s 10.5 medium would end up as a woman’s 12W.

You’ll find that shoe sizes vary by manufacturer, and it’s difficult to find the largest sizes in the store to try on. I recommend that you shop at an online store that gives you free shipping and free return shipping until you’ve figured out your size. Zappos and Endless are two great online shoe stores that do shipping both ways and have a good collection of large woman’s shoes, this page has a list with more stores selling large woman’s shoes.

Two Shoe Styles You’ll Love When Not In Stilettos

Now that you know how to find the right size shoe, I’m going to share two of my favorite shoe styles that are perfect for crossdressers. I know you all have at least one pair of pumps, so I won’t mention those again :)

Crossdresser High Heel Ankle Boot

Crossdresser High Heel Ankle Boot

High Heel Ankle Boot

The high heel ankle boot is perfect for crossdressers. You get the sexy feel of pumps with the extra support of the boot. The boot helps keep you steady if you’re just learning to walk in high heels, and the enclosed boot makes your feel look smaller. Be careful about boots with an overly pointed toe (the ones to the left are fine). If the boots end in a long thin point your feet will look longer than they actually are, because a few inches of the shoe are taken up just for show.

High Heel Wedge Sandals

High Heel Wedge Sandals

High Heel Wedge Sandals

Another great and comfortable choice is a wedge. These high heel wedge sandals are perfect for wearing during spring and summer. The wedge is much easier to walk on than stiletto’s, while keeping you feeling sexy. Watch out for straps that are too tight. Not only will this be painful, it will make your foot look like a squashed sausage – a definite sexy fail.

6 Comments | Also posted in Crossdressed Outfit of the Week, Fashion, Clothes and Shoes | Tagged | Trackback URL.

Makeup Tips Every Crossdresser Can Use

By Vanessa Law | Published June 2, 2010 | 9 Comments |

Dear Readers,

makeup-tips-for-crossdressers.jpg

Makeup Tips For Crossdressers

The week I spent at Esprit was a wonderful time spent meeting new people and discovering myself , but despite the hectic activity I was still able to learn a few novel makeup tips. If you’re new to crossdressing I recommend you start with the makeup basics for crossdressers , which will give you an easy overview of the basic steps to applying a fabulous face!

As I practice makeup application I’ve seen my skills advance from ‘not even a clown would be caught dead wearing this’ to ‘average girl style’. I’ve been helped along by every crossdresser’s makeup Bible – Making Faces by Kevyn Aucoin, as well as the endless video tutorials on Youtube. Though nothing can quite compare to consistent practice and critique. A light application of makeup every day (even in guy mode) has helped me hone the speed and skill at which I can create my canvas. In preparing my canvas I start with moisturizer, sunscreen, eye cream, concealer, foundation, bronzer, powder, a neutral eye shadow and sometimes lip gloss or lightly colored lipstick.

With your canvas set you can then experiment with different eye shadows, liner, mascara, blush and shades of lipstick. You’ll find that certain color combinations look good with your skin tone, and the interplay between your eyes, lips and cheeks will either be fabulous or dragulous.

Makeup Tips For Crossdressers

A few things I learnt at Esprit:

Feather the lip liner rather than coloring in the entire lip. When applying lip liner start by outlining your lips, then draw a few strokes down from the outer edges of your lips inward. Smack your lips together a few times to blend the liner over your lips then apply your favorite shade of lipstick. By feathering the lip liner you’ll prevent the lipstick from smudging while making it less obvious that you’ve applied lip liner.

Use two coats of mascara to make your eyes pop. Apply the first coat starting from the roots of your lashes, then leave it to dry. Once the mascara is dry apply a second coat to just the tips of your lashes. This is a quick and easy way to get a bit of extra length on those gorgeous lashes. I highly recommend Cover Girl’s LashBlast Mascara. I try to use high end makeup where possible, but I’ve yet to find a mascara that matches CoverGirl’s Lashblast.

Layer mineral makeup for greater coverage. I tend to apply fairly light makeup, and while I highly recommend Bare Escentual’s Mineral Makeup there are times I’ve wished for more coverage. A neat trick I learned is to apply mineral makeup in layers. Three or four light layers of mineral makeup will give you a lot more coverage without feeling heavy or flaking off. If you try to apply it all in one heavy coat you’ll end up with clumping, flaking and uneven coverage.

Start applying brush higher on the cheeks for a different look. I’m in love with the look where the blush is darkest near the hairline, but I had failed quite spectacularly to recreate it. The secret is to start the first application of blush higher on the cheek. The first place you touch will be the darkest, no matter how often you blend and fill other places. Now I start by brushing downwards from high on the cheek, then blend up until I get the intensity of blush I want. One nice benefit for crossdressers who are new to makeup application is that this approach makes it more difficult to look like a clown since most of the color isn’t centered on your cheeks.

Most importantly – there is no right or wrong in fashion and makeup application. Styles come and go, everyone has a unique features and skin tone, we’re of different ages with different personalities. Experiment and find what works for you. Not all of us can be as extravagant as Lady Gaga but that shouldn’t stop you from finding the style that shines you in the best light!

9 Comments | Also posted in Beauty and Makeup | Tagged | Trackback URL.

Is Staring Really A Compliment?

By Vanessa Law | Published May 15, 2010 | 10 Comments |

Today I had a few errands to run. I had to drop off the car at the mechanic, deposit a few checks in the bank and do a bit of shopping (My lovely wife rang the death knell for our water purifier last night). For some reason the mechanic always insists that you get there early, and for me 8am on a weekend is very early. After dropping my car off, I realized that nothing else was open for a good few hours – a perfect excuse to walk down to the local Starbucks and do a bit of writing while sipping a Grande Americano – my poison of choice.

On this lovely Seattle spring day, my wife had helped me choose a cool, comfortable outfit. A long flowing skirt, cami under a light long sleeved top and the open toed sandals I bought two weeks ago. On the walk down to Starbucks I noticed something curious – as they drove past men were staring at me. And not just me – I noticed one guy start his gaze with the woman jogger in front of me before smoothly switching and resting his eyes on me. I must admit, I had decidedly mixed emotions about this.

Five looks for a crossdresser

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Being Stared At While Crossdressed?

Very clearly there are different kinds of looks that we receive out in public. Over the last few months I’ve been working to decipher the different looks I receive, and I’ve figured out a few distinct reactions others will display to a transgendered girl.

Nothing to See Here – Move Along

This is not strictly a look reserved for crossdressers – we all come across this in our daily lives. It’s the momentary glance you receive as someone navigates around you, or interacts with you as if you were a regular woman going about your day. A good 95% of all your looks will be of this kind. People will treat you like another person, without any particular malice or attachment. It can mean you pass, or that you pass close enough the other person would feel awkward making a scene, or that you don’t pass and they don’t mind.

Point And Stare

By far the most feared look is the ‘point and stare’. This look can be accompanied by a derisive facial expression, or in extreme cases slurs or even violence. This look is mainly shown by men when they figure out that you’re not all woman, and can’t help but let their displeasure show. You’ll know this look when you find someone looking at you in a ‘hard’ way, with an unwavering gaze. They won’t seem the least bit embarrassed when you notice them staring. The best advice I can give is to smile and move on.

Something Strange is Afoot

This is ‘Point and Stare’s’ tamer sister, and is often difficult to distinguish from ‘Checking You Out’. If you notice people looking at you out of the corner of your eyes, or quickly averting their gaze when you look at them you could be dealing with ‘Something Strange is Afoot’. The surest way to tell when you’re receiving this look is when you watch it transform before your eyes from ‘Nothing To See Here’. This can happen when you speak in a not so feminine voice for the first time with someone. You’ll see a moment of confusion before they compose themselves.

Checking You Out

This can be a pleasant experience, since it validates you pass well enough to satisfy a hormone soaked male. Though it can also be a little off putting after a while since you can feel like a piece of meat on display. Depending on your paranoia level you could easily mistake this look for ‘Something Strange if Afoot’.

One sure way to distinguish the two is if you notice the same guy’s attention lingering on another woman a moment later. He’s a serial looker, and you just happened to be on his look list. A corollary to this is if you find his gaze transfixed on a part of your body that’s not your face. He’s a serial looker, and your face is somewhere near the end of his list.

Another way to tell is to watch how other woman react. Woman are usually the first to give you very subtle hints that you’re not fully passing. If other woman aren’t bothered by you in any particular way you can be sure that you haven’t been outed. Trust me – men see what they want to see, and it usually doesn’t extend much beyond the pleasing feminine figure.

Solidarity Sister

This is by far my favorite look, and is reserved exclusively for visual conversation with other woman. It affirms my femininity without making me feel cheap or used. For a moment you catch her eye – you smile and she smiles back. You acknowledge each other’s passage through womanhood with a brief show of support, of recognizing each other’s worth and humanity. Sometimes this is the start of a conversation – a few moments of connection in a world full of strangers.

This look doesn’t mean that you pass – it means that you’ve been accepted into her circle of fellow woman. If she’s recognized you as a man, she’s also acknowledged and accepted your femininity.

What other looks have you received?
Have you found any other ways to decipher them?

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