When I see the term passing, I wonder does this mean in public everyone thinks I am actually a biological woman or that they accept who I am without questioning “why is that man dressed like a woman?” Certainly we do have the desire to pass some sort of mythical test to blend in and to have everyone identify us as female. Not only is it about our mannerisms being feminine, dressing appropriately, and our perception of ourselves; makeup is a key factor in helping us achieve our confidence as well.

Something I picked up from my daughter-in-law that really made me think. She passes time – you know those bored moments when there’s nothing going on and nothing to do –by watching makeup YouTube videos and trying out the techniques and looks that she likes. Sometimes she will do 2 or 3 different looks in one sitting.

 So that got me to thinking, how do biological girls get to their signature look, or say their everyday look? I’ve discovered that it is all in practice and peer reviews. Most girls start at around 12 or 13 (some earlier), parent approved or not. They learn from one another, and critique one another. By the time they hit their 20s they’ve pretty much nailed down the signature look and by the time they hit their 30s their makeup style and technique are pretty much second nature. This phenomenon is not limited to the internet YouTube generation. This has been going on since the advent of the modern teenage girl. I remember my mother talking about when she was a teen in the 40s. So my guess? Since the popularity of girls wearing makeup.

 The difference for many of us in the transgender/CD world, is we don’t know where to start, we don’t know what might look good, and many of us start much later in life without that female influence. What we need is trial and error time, critiques from our peers and women who’ve been at it a while, with lots of practice to get to the point where it becomes second nature. It’s much like dressing, we find what fits, what styles look good, and discover that while heels make us look very sexy, they’re not practical for everyday use. Makeup is really no different; there’s the day look (you’re everyday look), out clubbing look, the sexy sultry look, the possibilities are endless. But like all girls we need to figure out what look is appropriate for the occasion, so you’re not sticking out like a sore thumb by looking sexy and sultry at the grocery store.

I’ve been trying my daughter-in-law’s technique for about a year now, granted not diligently. However, more recently I’ve been experimenting with eye shadow almost every night. The look I have on my profile picture took a lot of doing, but now I’m much faster and getting better at it. Still can’t do eye liner worth a dam, but it’s best to tackle one thing at a time.

 My daughter in-law came over to hang out the other day, so I decided I’d do some makeup and see what she thought. Before she got here I put on foundation, a little blush, and did a simple day makeup look I got from a Lancôme video. I had no wig, and was dressed in my male attire. Much to my joy she was very impressed with my look and said I look very nice.

 So there it is ladies, if you can impress the girls, you’ve got it down. The key to success like any art is practice, practice, practice. 

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Darcy Bainsley

I love expressing my femininity, everything from just the subtle things that only I know about, all the way to all dolled up and out on the town. I try to focus on enjoying small triumphs and the little things in life that make me happy and feel pretty.

Latest posts by Darcy Bainsley (see all)

  1. Cloé (CC) : 1 year ago

    Love this topic and the comments all have made. The power of makeup was lost on me until I started to try it about a 8 momnths ago. Utoob is my advisor, but I find it overwhelming sometimes. My wife is uncomfortable helping, but did give me the best advice so far. “Use just a little and blend it in, you don’t want it to be too noticeable”. Well damn if she wasn’t right, but it took me a long time to figure that out. I had been so focused on covering up the naturally dark circles under my eyes that I looked like an ad for Bisquick. The dichotomy of trying to be light handed while trying to cover those up was the challenge of a year. My profile pic is the culmination of that effort. I was so giddie with the results that I finally took my first Cloughie selfie. I even forgot to do my lips – LOL . Now to figure out the eyes and contouring that nose!

  2. Dwight Richardson 1 year ago

    Hello all you hottie , I am just 7 months of trying to accept and mold myself into a lovly crossdresser I have bought some nice c cup breast forms and like to go out to gay bars dressed up . but my makeup skills need work its fun trying new styles and I love going out shopping for high heels and dressed and different wigs. Well got to go its makeup time Love Dedi

  3. Billy mcglathery 1 year ago

    It hard to good help with learning how to put on makeup I went to Ulta and they taught me a lot plus I think the technician was as thrilled as I was and I look totally hot when I leftand where I am today wearing full makeup all started when I was younger with the lipstick I still love lipstick to this day I said you never can put on too much lipstick and lipgloss but maybe that’s just his naughty girl side of mekeep on putting it on nice and thick good night Merry Christmas I love every one of y’all

  4. Teri 1 year ago

    Eyes….that is my focus for next few months…..i’ll worry about foundation later

  5. Georgii 2 years ago

    Ru Paul has great tips to help you with your skin, makeup, and all things girl..

    UTUBE yes sweetie UTUBE

  6. andrea 2 years ago

    I’m still terrified of doing my make up seem to spend hours trying and not getting anywhere

  7. Sallysim 2 years ago

    How very true Darcy, I was terrified of doing my makeup and still are to a certain degree, although I’m quite happy doing my everyday look and quite quick at it now. I struggle a bit with my special look especially my eye shadow and lips, just can’t seem to get them right, but I’ll keep on practicing and I’ll try watching YouTube lol.
    Thanks for the advice Darcy

  8. Karyn Lobelia 2 years ago

    I was extremely shy about doing my makeup and terrified I would look like a clown or look ridiculous . I started out by letting my wife do my makeup and only carrying lipstick in my pocket or purse . Later I did makeup
    at the Estée Lauder counter when they videoed it and learned to practice at home . I watched a lot on YouTube and came eventually to DOUNG my own makeup as a natural part of being femme . I had to overcome being afraid of some commenting on my makeup . I like to tell everyone to try simply to wear what is appropriate for the time of day and where you will be so that you can be yourself but. Not stick out from other ladies in that situation . Always coordinate your makeup and nails with the color of your clothes and the indoor or outdoor lighting you will be in and remember to always look back one more time at the mirror before you leave , no one thing in Jewerly or makeup should Just Jump Out as app posed to the total look .

    • Stephanie 2 years ago

      Karyn thank you very, very, very much for so much sharing with us and for your very wise advice! You are very inspiring and…..stunningly gorgeous!

  9. Very nice article Darcy. Practice, practice, practice. It’s how you get better at everything (as long as you get honest critiques)! I’m still looking for a “signature style”, but I know I won’t get there without putting in the time.

    Keep writing!

  10. Author
    Darcy Bainsley 2 years ago

    Thank you ladies for your kind words. Reading the comments, I see I may have left a few gaps (only so much you can say in 700 words 😉 ) So I’ll try to fill the gaps with a few tips.
    1. YouTube videos – look at the ones from professional artists, especially those from product manufactures. Yes they are selling the product but also showing you how to look your best.
    2. Brave out to the dept. store makeup counters, such as Macy’s. Look at MAC, Lancôme, Bobby Brown, etc. – Yes the are more expensive than drug store cosmetics but the results are much more fabulous. Ask the sales rep questions. Be bold “Yes it’s for me”, “How do I?” Don’t be afraid. They are very friendly, very knowledgeable, and very helpful.
    3. Get some other girls together, or just yourself. Locate a Mary Kay rep that does makeovers and have a makeover party.
    4 This I think very is important – start simple – Learn foundation (and for us bearded ladies – concealer), blush, lipstick, and simple eye techniques. Simple looks you can memorize and master easily.
    Remember keep it simple and practice, practice, practice

  11. Samantha G..... 2 years ago

    Great article Darcy. The makeup is an integral part to dressing up for me.
    I’m always looking for tips and tricks to make it look better.
    I hope one of these days I’ll have it down to 20 minutes & done.


  12. skippy1965(Cynthia) 2 years ago

    Darcy-lovely article from a truly lovely woman! I have a fairly minimalist look which I dress up or down depending on which colors I use for the eyes and lips. So wish I had learned all this when was a teenager though-along with styling hair as well!

  13. David 2 years ago

    Yes I agree my make up looks second rate and I have decided to go to a professional make up artist to get help if anyone has a great you tube site where I can learn the craft it would be most appreciated have a great day looking forward to hearing from the community Danni

  14. Janine 2 years ago

    It seems to me that some days are better than others when it comes to applying my makeup. Sometimes after I have applied it and I look at myself I know that I’ve nailed it perfectly.
    However there are other days when no matter what I do it just doesn’t seem right.
    As far as I’m concerned makeup is the icing on the cake when it comes to passing as a female.
    When I read your article on makeup I couldn’t agree more with you about practice practice practice.
    The more you do the easier it gets at least I think so.
    Thank you for bringing it out in the open.
    I’m sure that there are a lot of girls who would agree with you as much as I do.
    Looking forward to seeing your posts in the future

  15. JaneS 2 years ago

    Very true Darcy, practice, feedback and revision. What sort of feedback is also important. We need honest feedback but that doesn’t need to be brutal. For example, I’d prefer “What sort of concealer do you use?” to the “You ought to try using a concealer.” that I got from a so-called transgender ‘friend’.

    My wife is the Mistress of Subtlety (or the iron fist in a velvet glove) so she lets me know what looks good and what doesn’t. She is getting less critical these days which I take as a good sign.

    Practice, practice and more practice – and never think it isn’t worth the effort.
    Thanks for a great article Darcy.

    • skippy1965(Cynthia) 2 years ago

      JAne-your wife sounds like she was a lot like my mom was! Could tell you go to hell while making you look forward to the trip! She always told me that the best “insults/criticisms” are the ones where the person doesn’t even realize they are being insulted/criticized) but she was also the kindest sweetest woman I knew!

  16. ane 2 years ago

    Makeup & feminine manerisums are the hardest parts to master for me–
    Wife Tries to help—But she grew up in a highly religious home & has never wore much makeup(she was one of those kids that didn’t sneak behind mom & dads backs to learn with girlfriends)—So–knows little more than I do-
    It has & is a struggle learning this stuff—Watching(& understanding ) the stuff online (So far) is not helping-
    Jane–London Ontario

  17. Janet38 2 years ago

    I love doing my makeup. I’ve tried all sorts of looks. I do my lipstick last just to see how it pulls everything together. I’m working on my Rockabilly Girl look. I know it’s mot practical but I just the look of “Hey. I’m all woman” it gives me. Female Pride I guess. But I truly love being a feminine woman in all ways.


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