Essential makeup tips for crossdressers

Dear Readers,

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) will help hone the speed and skill at which you can create your 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

Makeup Tips for Crossdressers

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 Natural Mascara. I try to use high end makeup where possible, but I’ve yet to find a mascara that matches CoverGirl’s.

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!

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Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.

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  1. Rachel Taggart 7 months ago

    Thank you for this. I adore wearing makeup and like every woman it makes us feel more confident and feminine. You can relate this topic like anything we do in life, the first time you try anything new it is very strange very challenging but the more you apply (pardon the pun) and practice it becomes more natural and a bit easier more comfortable and confident. But ladies we must have fun while we are trying

    Rachel x

  2. Samantha Louise Scott 2 years ago

    Very good advice all round.

    One thing I have been doing for some time now is the two layers of mascara trick. Not the same one twice though. As it says , use good quality but I find it best to apply a lengthening one then use a thickening one.

    Got to be careful you don’t get the dried up inkwell effect but if its done right, the result is absolutely fantastic and much more natural than falsies.

  3. VickieJ 2 years ago

    Great artical with some very good tips. I just ordered the book.

    I’ve never had facial hair and have never needed to shave (not sure why) However, applying my make up correctly has been a challenge to say the least. Twice I have hired someone to apply and teach me the process. So far, that helped but was not the total answer. I think as the artical points out ” practice” is the answer.

    Thanks for this artical. I’ll keep practicing


  4. Tiffani 2 years ago

    Fellas who of you play Pokemon GO? Amazing game, finally Farfetch’d has been caught using pokebusterbot.
    With this bot you can catch pokemons on autopilot!

  5. Cindy 2 years ago

    I love the advice and help you all girls give . I need help in the makeup Appalachian . No help hear at the house . Thank you the weab site . It my gate way to girls woo feal like I do . Thanks.

  6. Terri 2 years ago

    My recommendation is to go to a cosmetic counter in a dept store. I go to Estee lauder in Macys. Get a makeover. It is free if you buy one item. If you don’t feel comfortable doing that call a mary kay rep.

  7. Erica 2 years ago

    I have difficulty with my eyes. Eyeliner and eye shadow my drawbacks but I keep trying.

  8. Sawan Kumar 3 years ago

    Hello I’m a man of my body is stocky guy like I am a woman I want to be like you see how it would be possible for all sorts of things I will need ?

  9. Karyn Lobelia 3 years ago

    My wife started me wearing makeup , and what I learned was to wear makeup to enhance the clothes you will be wearing in the light setting you will be in , for example you can easily learn what looks beautiful and natural in different types of light . Your makeup should reflect how you want to present yourself . At work , I wear a little more makeup than my co workers , but that is because I am really more feminine than a lot of my lady fiends . But I want to blend in when we go out for lunch . t the ballet , opera, or similar social events such as charity balls I really love my wife when she gives me the gorgeous glamour girl look . We usually look at videos on YouTube and we go for a bridal look or a supermodel with high cheekbones , or sometimes the Bardot look . We giggle and have fun seeing how close we can match the looks on YouTube . Of course make sure you have the same or similar skin tone as the model . I could never try a Megan Fox look , but the Tippi Hedren or Grace Kelly old time gorgeous makeup is what I love , because I love being complimented on being glamour it’s as if it is only natural . I love flattery , of course I love to compliment my friends SINCERELY on how they look . I is really all about fitting in , being yourself , and being sweet to all the dear people in your life . Love gives you an inner glow that makes you eyes sparkle and say I am so glad to meet you . We may not have a trail to wag , but we can always smile when we meet people .

  10. rogina garter 8 years ago

    One thing that helps me blend in the layers of required coverage is to Spritz my face with a citrus based hydrating spray after the mineral powder. This blends it all together and eliminates the grainy look. Spritz,use a little fan to dry,wait a minute, and put a spritz of Mehron sealer on[prevents stains] then go for the eyes and when done,your cheeks are ready for the blush. Do blush right,all is great…wrong..then you get the clown look!! When I was lasered,it was so great to need such little coverage. But now I am back to needing it again so blending it all together really helps.

  11. Kristina 8 years ago

    Thank you so much Meghan i just ordered the book , im still searching for the right skin care regime for me but things are moveing along nicely thank you for your help

  12. Meghan 8 years ago

    It all starts with what you do between shaves. Your daily skin care routine is just as important as shaving. I use an anti wrinkle serum all over my face let it set for 5-10 minutes, then moisturizer. I generally apply more to the shaving area than other locations on my face. I also moisturize in the evening 2 or 3 times a week, although it is recommended that you do it nightly. I have found that since I started doing this I have been able to shave even closer than I ever had. Although this works for me, if you need a more stringent skin care regime, I recommend buying Bobbi Brown's Makeup Manual and reading chapter 3 about skin. It covers everything from lifestyle to skincare basics to cleansing and moisturizing. The bonus of buying the book is all the makeup info that's in there!!!…hope that helps.

    • emily 3 years ago

      if you use E Lauder Doublewear makeup the beard is disguised for a number of hours

  13. Kristina 8 years ago

    i would like to see some tips on what i feel is the hardest part of being a girl , Facial hair , i dont care how good your make up looks or how sexy your outfit is, the bearded lady is just not gona cut it . i know hair removal is an option but what if thats not affordable. i have tryed all kinds of shaving creams, razors and so on. i still find some stubble and at times i brake out. would anyone have any tips or tricks to help?…K

    • anna 8 years ago

      No advice, but I know how you feel. I'm saving money for Electrolysis, but that's still a long way off. Any foundation heavy enough to conceal my beard (I have dark hair / fair skin, so even after a fresh shave it is obvious) is also too heavy to look any good on my fair skin.

      Of course, I gave up on passing and just started presenting as a woman as best I can (at least, when I'm not at work)… but a solution to this would still help me quite a lot.

    • Vanessa Law 8 years ago

      Sorry I can't help you too much love. It's been a long time since I had to shave my face.
      The best I can recommend is a good beard cover that has a tint to it to hide any stubble.


    • Tracy 8 years ago

      I've used Dermablend. It can be found in certain dept. stores, i.e. Macy's, Belks, etc.

    • Ambersinclair69 3 months ago

      Beard cover with orange color to cancel that five o’clock shadow

  14. Leslee 8 years ago

    I really need a hands on teacher to help me with makeup. No matter how many Utubes I watch I like someone to talk me through new ideas on makeup in person. I think Ill go for a make over but have her talk me through the process so I apply it the way she she wants. I've always been a hands on person and makeup is no different in my learning applications. I like to experience new products and their applications and I'm always ready for new ideas. I dont know if this is just vanity but every girl likes to look her best.

    • paula2062 6 months ago

      I found that you can use red lipstick on beard area then foundation. This seems to work.

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