Makeup Mistakes Crossdressers Can't Afford to Make

Take heart fellow crossdressers – genetic girls make mistakes with makeup as well! Sally did a good job listing the 12 makeup mistakes to avoid, and if you read nothing else in this article you should take heed of these words from Jessica Liebeskind, a New York City makeup artist:

“Makeup is a wonderful tool to enhance your look, but used correctly, it should never look fake or like you’re wearing a mask.”

I’ll take a gander through some of the mistakes, and share my thoughts on how these makeup mistakes apply to the crossdressers among us as well.

Wearing too much (or too little) makeup

I don’t know about you girls, but I’ve never been accused of wearing too little makeup 🙂 I think a major problem crossdressers face is wanting to hide their face behind a mask of makeup. Whether it’s stubble to be covered over, or just an over exuberance with the newly discovered paint jars we need to be careful to tone down our makeup. Remember, you with makeup should be you, only better.

Using the wrong color foundation

I think we’d all like to get this one right. For crossdressers though it can be tough to walk up to a makeup counter and start trying different shades. If you’re nervous of doing this at the makeup counter in a department store try asking your hair stylist. Often hair dressers are trained in cosmetics as well and can help you select the right shade. You might also feel more comfortable going to a beauty school to be color matched, where the atmosphere is decidedly more liberal.


If you’re still weary of these, try buying three shades of foundation, one the color you think matches, and a darker and lighter shade. See which matches best at home but keep the others. Your skin will get lighter during the sunless winter months, and sport a golden bronze tan during summer so you can put those other shades to good use.

Crossdressers not caring for their skin

I can’t say enough about this – Moisturize, moisturize, moisturize! I’ve seen many girls who would pass tremendously well if only they had dipped into the moisturizers more liberally when they were younger. Your face is the first thing most people will see, so treat it with care and love. What about the crossdressers who haven’t taken care of their skin? There is still hope – there are many innovative new facial treatments from dermabrasion to laser resurfacing that will roll back the years. As with any procedure you need to carefully evaluate the risks and speak with a qualified dermatologist.

Crossdresser Party last night and the makeup is still on?

Yikes! Don’t go to bed with your makeup on! Your average crossdresser probably never got good advice from your mother to remove your makeup before going to bed. Now you have no excuse – just do it hon.

Sally has a few more tips to share – good luck, and look fabulous!

P.S. Still flummoxed by makeup technique? Discover the makeup secrets of Hollywood stars and go from drab to fab


More Articles by Vanessa Law

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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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14 years ago

I am just starting out as a make up artist and I also sell make up. I find that over half of my clients are either cross dressers or transgender. It makes it much easier to work with one person on a one on one level, then to go into a store filled with people. The company that I work for trains you on skin tones and we are taught how to perfectly match make up to each pesons needs. If anyone is interested in learning more about it, they can contact me. Just thought that I would give everyone… Read more »

Evett Jerry
Evett Jerry
13 years ago

Is there something out there that can be used to fill small forehead wrinkles? Something that makeup can be applied after.

Is there a way to make your top lip bigger using tape to pull up on it? I tried it. I placed one end to the top line on my upper lip. by pulling the tape and taped the other end inside my nose hole. Worked….. But you can see the tape. Duck tape and makeup……doesn’t work. It was fun..

Evett Jerry
Evett Jerry
13 years ago

I found out, that I was trying to hide my face with makeup. That I found out that a little eye detailing, touch-up here and there, plus lips. Makes me want to be ME. The color of my skin is a good back drop. I stopped trying to be a 10. I am a man dressing like a girl……I’ll learned to settle for a 6. I found out when I worry more what I look like, I feel people look at me more. When I paint my face less, wearing something not so fashioned, Maybe jeans, crazy hat, and off… Read more »

11 years ago

As an International Designer of Make up, experienced by many of my private crosdreesers,transgenders,,,,,my modo is LESS IS MORE.
Dont make make up obvious, will not work…..
In my one on one classes I always said about areas,define, hide, highlite…look real and BLEND a mua secret for generations…….
Choose the right wig, dont try to be a California girl, be the woman that you are inside, sometimes modern hair do’s Just Work.
And when become to clothes dont try cha cha…doesnt work
E-mail me for ALL SECRETS…..ciao

Brittany Travis
Brittany Travis
6 years ago

Im a straight male who loves dressing up all girly once in a while. These make up tips may just come in handy. I cant wait until I gain the courage to go out in public all girly and tell everyone I know. Im just afraid of people shunning me out. Im not gay although may be hard to believe with me wearing cute panties and bras with dresses and skirts. I just love the feeling I get when I crossdress. It makes me feel notty and like a bad girl. I like being a guy but I wish I… Read more »

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5 years ago

Back in high school I learned how to apply Eyeliner also Mascara, Because I was a Heavy Metaler …..I loved wearing makeup so I had to learn how to apply it

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