Should You Give Up Your Goal of Passing as a Woman? (For Crossdressers and Transgender Women)


“Passing as a woman” is the Holy Grail for many crossdressers and transgender women.

But it is really a goal worth pursuing?

If you’ve been afraid to show your feminine side for fear of not “passing,” it might be time to rethink your priorities.

I believe everybody has the potential to pass, but let’s face it… it’s not always easy!

It could take years to master all the subtleties of walking, talking, and presenting yourself as a woman. You might even require surgery to be truly passable in all situations.

That means that unless you plan to live as a woman full time, trying to become 100% passable just isn’t practical.

Rather than getting hung up on passing vs. not passing, I suggest you make it your goal to “blend in” instead.

Blending in means you look feminine and harmonious enough not to stand out in a negative way – even if you aren’t 100% passable.

Most people don’t scrutinize everybody around them, so unless there’s something glaringly off about you, you are unlikely to attract a second glance.

Does this mean everybody will think you are a cisgender (genetic) woman? Probably not. But it doesn’t matter.

The happiest crossdressers and transgender women I know don’t care whether they pass or not. They care about being themselves.

Passing is great when it happens, but there’s nothing wrong with being seen as the classy crossdresser or transgender woman that you are!

As long as you choose the right environment and present yourself well, you are likely to be met with acceptance.

Now I’d love to hear from YOU!

Please take my “Passing Poll” and share your thoughts below!

Why do you wear high heels?


The truth is that wearing high heels can be an adventure.

Walking gracefully in high heels is a learning experience. Once you learn how, usually after a lot of missteps, you still have to deal with the potential pain.

At the end of a high heel session, your feet often hurt. And depending on your feet and your shoes, the pain may begin after eight hours or after one hour. Yet, many of us will continue to wear high heels no matter how much pain we may experience.

Some wise man once defined insanity as "doing the same thing over and over again and expecting different results."

So are high heel wearers insane?

I will admit that when I slip on a pair of heels, I hope the experience will be pain-free. And sometimes it is, yet at the end of the day, I am still happy to remove my heels!

Abby of Vivian Lou fame mentioned that the former editor-in-chief of British Vogue Alexandra Shulman said, "Wearing a heel gives you a completely different feel about your body. In my case, it makes me feel in control."

Abby added, "Dolly Parton has said she wears heels to lift her spirits, shoe designer Charlotte Olympia Dellal wears heels to feel taller, sexier, more confident, powerful, and glamorous, Harper's Bazaar global fashion director Carine Roitfeld wears heels to move, sit and speak differently, fashion designer Monique Lhuillier wears heels to feel empowered and rocker Lita Ford wears heels for attitude."

Like they said and I wear heels because my mother was my role model. Whenever Mommy dressed up, she wore heels. So whenever I dress up, I wear heels ("like mother, like daughter").

What's your excuse? Why do you wear high heels?

Are You Too Old to Crossdress or Transition as a Woman?


Every now and then, I hear somebody ask…

“Am I too old to crossdress?” or “Am I too old to transition as a woman?”

The simple answer to this question is NO.

Whether you are 33 or 73 – and whether you aim to express yourself through crossdressing, or live as a woman full time – it’s NEVER too late to be your true femme self.

Life is short and you deserve to make the most of your precious time on earth.

Does this mean you should act on every frivolous whim that crosses your mind? Of course not. And obviously, life-changing moves like hormones or surgery need to be given serious thought.

But I believe the true desires or your heart are meant to be expressed – no matter how long they’ve been buried.

In fact, embracing your feminine side can give you a whole new lease on life. I see it all the time: People seem to grow years younger when they make the decision to be themselves fully.

Having the courage to express your true self also inspires others to do the same. The world needs more of this!

In the words of Laverne Cox, “It is revolutionary for any trans person to choose to be seen and visible in a world that tells us we should not exist.”

I’ll say it again: You are NEVER too old to be your true femme self.

So go for it, girlfriend: Buy the shoes, schedule the makeover, contact the gender therapist – or do whatever it is that you’ve been holding back on.

You deserve it. And it’s not too late.

Do you agree that age is just a number?

Now I’d love to hear from YOU on this topic …

How old were you when you decided to embrace your fab femme self? (Or are you still waiting?)

Let’s continue the conversation in the comments below!

High Heels Forever!


I love high heels! So much so that I own over a 100 pairs.

The second piece of woman's apparel I ever wore were my mother's high heels (after I slipped on a pair of her nylons). Since that initial crossdressing experience, I almost always wear high heels when I present as a woman. Occasionally I joke that this whole transgender thing is just an excuse to wear high heels.

Without a doubt, wearing high heels is the most difficult thing about presenting as a woman.

Walking gracefully in high heels is an art.

And then there is the pain! Wearing a girdle, waist cincher or clip-on earrings can be painful at times, but you can almost always count on wearing high heels becoming a painful experience sooner or later.

Despite the drawbacks, I'll give up my Louboutins when you pry them from my cold, dead hands.

Abby of Vivian Lou fame feels the same way and she offers some tips in her blog to make your high heel experience as painless as possible.

👠 How to stop feet from slipping forward in high heels.

👠 How to walk up and down stairs in high heels.

👠 Why not to wear the same pair of high heels every day.

As Abby says, "Here's to high heels without the hurt!"

How to Walk in Heels: Lessons from the Stiletto Whisperer

Perhaps this model needs to take a high heel walking class with the Stiletto Whisperer?  High heels can be a quick and easy way to dress up your outfit, but Victor Chu, a former footwear designer in New York dubbed the "stiletto whisperer" claims most women are wearing them incorrectly. "Women think heels are sexy because men think they're sexy," he told the New York Post. "But, you see a woman wear this pained expression and shuffle. I've seen guys giggle at them - it's not sexy. Bottom line is, you need to be fit to walk in heels with stability."

Chu once developed comfortable shoes for Uggs and Reeboks, and teamed up with dancer CeCe Chin in 2006 to create the high-heel fitness routine, Legworks. This summer he created a series of personalized classes in New York for women to perfect their walk in their high heels. We reached out to get the inside scoop and tips on how to properly walk in high heels with minimal pain.

"We tell [students] to bring two pairs of heels to the class: ones you wear everyday and the ones that you want to wear," Chu told Yahoo! Shine. The private classes start at $50, and Chu tells Shine that 60% of the class is perfecting your walk. "New York City is the capital of high heel shoes and fashion," Chu told Yahoo! Shine. "Out of anywhere in the country, women wear heels everyday here. It's easier for guys when they get dressed up because they just put on their dress shoes and start walking. There are essentially built in problems with heels and this is the main reason why we offer the course." A recent survey released by The College of Podiatry, more than 40% of women say they suffer through the pain of wearing heels for the sake of fashion. Most women report that heels start to hurt their feet after an hour and six minutes of wear, while 20 percent say that they can feel the pain after just 10 minutes. According to researchers at the University of Portsmouth, heels can change the way the entire body moves, including the pelvis, hips, legs, knees, feet and even shoulders, to emphasize femininity. The researchers, whose study appears in the scientific journal Evolution and Human Behaviour, say men rate women wearing heels as more attractive then those wearing flat shoes. Chu feels all types of women young and old could benefit from his classes, and that no one should be bashful about coming in. "We have a lot of overweight women who take the class, and there's no reason why they shouldn't be able to wear heels," he told Shine. "It's just a matter of adjusting the heel height and type of shoe. We don't criticize or make anyone feel unwelcome."

For those who can't attend Chu's personalized classes, the footwear expert shared five tips you can incorporate into your heel-wearing lifestyle today:

1. Make sure your heels really fit. Often we force our feet into improper shoes because we bought the wrong size or a style that isn't comfortable or stable. "There are literally thousands of styles to choose from," Chu advised when asked about shopping for heels. "A good fit means that it's snug on your foot. if you have wobbling at the ankles or the fit is bad, go for more coverage around the foot like thicker straps instead of thin straps."

2. Check your soles. Make sure that the sole of the shoe is completely flat to the floor and doesn't tip over or wobble. "This will help to give you a lot of stability," he said. "Avoid those shoes that have a 'boat bottom,' meaning it's not completely flat to the surface of the floor."

3. Improve your core. "It will give you tons of control when you're walking, and that's important for keeping your back straight and providing stability and control when walking," said Chu.

4. Posture is everything. Remember to keep your head up high and your shoulders back.

5. Look straight ahead. When walking down the street, always be aware of what's ahead of you at least 1/3 of the way down the block. "Look ahead, not down," Chu said. "If you're looking down, this means your shoes don't fit well. There shouldn't be anything hurting or pinching."

Checklist: 10 Elements of a Flawless Feminine Image (For Crossdressers and MTF Transgender Women)

There are so many details that go into creating a beautiful, feminine image:

Clothes, hair, makeup, shoes…

The list goes on and on!

To help you keep track of everything, I’ve put together a Flawless Feminine Image Checklist.

Can you answer “YES” to these 10 questions?
If so, you’re ready to share your fab femme self with the world!

BONUS CHECKLIST: Click here to download a 1-page PDF version of the checklist that you can print out and keep with you.

1. Is your makeup appropriate?


Many women (including crossdressers and transgender women) overdo their makeup. Before you step out en femme, be sure you haven’t made this mistake.

Light, natural makeup almost always looks better. There are two exceptions to this rule:

  • If you have dark coloring, you can go for deeper, bolder shades.

  • If you’re going out at night, you can wear higher intensity makeup.

2. Is your hair shiny and freshly styled?


Beautiful hair is important part of your overall image. To soften masculine facial features, choose a hair style with soft waves or layers. Stay away from angular styles.

Shiny hair makes you look sexy and youthful, so use a smoothing serum if you have dry or frizzy hair. I like Pantene Pro-V Smooth Serum.

If you wear a wig, be sure to wash it regularly and use a finishing spray like Revlon Finishing Spray for Synthetic Hair.

3. Are you wearing the right shapewear?


The size and shape of your body broadcasts your gender to the world. (No surprise there!) Are you wearing the right undergarments to create your best feminine shape?

At the bare minimum, you should own these items:

  • Breast forms
  • A well-fitting bra
  • Girdle or shaping camisole
  • Panties (regular and padded styles)
  • Control top pantyhose or tights

While you don’t need to wear all of these pieces at once, it’s good to have them on hand in case you need extra shaping to go with a certain outfit.

4. Are the proportions of your outfit correct?


Proportion refers to the way your clothes work together in length, width, size, and volume.

Pairing two similarly-proportioned items together can be disastrous. For example:

  • Short Skirt + Short Top = Slutty
  • Long Skirt + Long Top = Dowdy
  • Full Skirt + Full Top = Heavy
  • Tight Skirt + Tight Top = Sausage

Your clothes should balance each other out. For example, if you wear a tight top, pair it with a fuller skirt.

5. Are you wearing the right accessories?


Accessories can make or break your outfit. Too few accessories and you look underdressed. Too many and you look like a Christmas tree.

Your accessories should also be in harmony with your body proportions. If you’re full-bodied, avoid dainty accessories like tiny earrings or a delicate bracelet. Instead, wear heavier, thicker pieces that go with your size.

6. Are you wearing the right shoes?


Shoes say more about you than any other accessory, so pay attention to this detail. Here are 3 things to consider:

  • Do your shoes suit your outfit and the occasion? Wearing shoes that are too casual or too formal is a common mistake.

  • Are your shoes proportionate to the size and shape of your feet, as well as your overall body size? When in doubt, go for a classic style with a rounded toe and heels that aren’t too thick or thin.

  • Can you walk in them? If not, wear a lower heel until you’ve mastered your walking skills!

7. Are you carrying the right bag?


Choosing the right bag is critical.

First and foremost, your bag should match the formality of your outfit. If you wear a casual bag with a fancy outfit, it cheapens your appearance. Wearing a fancy bag with a casual outfit looks silly.

Second, be sure your bag is works with your proportions. If you have a large build, a tiny handbag will make you look even bigger by comparison.

8. Do you smell good?


Your image is made up of more than just the way you look. It also includes details like the way you move, sound, and yes, smell.

Smell is an important detail because scent is strongly linked to emotions. You aren’t fully dressed without perfume, so choose a scent that makes you feel fabulously feminine.

A word of caution: don’t overdo it! Unless somebody is close enough to hear you whisper, they shouldn’t be able to smell you.

And if you’re going out, don’t forget about your breath! Brush your teeth and carry gum or mints with you.

9. Have you removed all excess hair?


We all know that smooth, silky skin is sexy and feminine. Double check that you don’t have any stray hairs or stubble left behind before leaving the house.

It’s easy to forget all the hairy spots, so here’s a quick checklist:

  • Beard
  • Nose
  • Ears
  • Underarms
  • Forearms
  • Knuckles and fingers
  • Legs
  • Toes
  • Bikini area

10. Did you check yourself from behind?


You wouldn’t leave the house without checking yourself out in a mirror, would you? Well, don’t make the mistake of only viewing yourself from the front. Remember that you also have a back side!

Use a hand mirror to view your reflection from behind. Does the back of your hair look good? Do your clothes fit properly? Do you have any toilet paper sticking out of your skirt? (Just kidding!)

It’s all about the details

If you answered “yes” to each of the questions on this checklist, then congratulations! Now it’s time to step out and enjoy your flawless feminine image.

Be sure to keep this checklist handy so you can refer to it each time you present yourself as a woman.

As always, I’d love to hear your thoughts. Is there anything you would add to this list? Please share your comments below!