When I first took those steps to transition and begin my new life going forward there were so many questions and concerns. While I had been going out in public, it was to attend events or go to clubs and I could dress for those few hours out in settings that were more forgiving or accepting than say running to the grocery store or going to work. The makeup and outfits I wore were not going to necessarily work and I found myself wondering how I would learn a whole new approach in applying my makeup so it looked seamless and blended. Which colors worked for my skin tone and how will I look after eight hours at work? I knew I had the basic techniques down but I was really lost at making it all come together. I had begun electrolysis and laser treatments earlier in my transition and was fairly pleased with the results. Still, I had been applying thick heavy concealers thinking it would address what I considered areas of imperfections. I didn’t realize I was actually causing them to be emphasized more.

I finally broke down and asked for help from two female friends from a church group I belong to, who knew I was transitioning. They agreed to come over to look over the products I was using. I quickly learned from the two of them that I would have to incorporate a whole new regimen for putting on my face. They started by going through my vanity and had me start by throwing out the hodge podge of products I had bought which were mostly your basic drug store brands. They wrote down a list of branded products like MAC, Lancome, and Sephora for me to try out when I visited the mall and emphasized I should consult the women at the counters to also have them provide recommendations for a proper skin treatment routine that worked with my complexion telling me that this would be the most important thing to religiously follow. They also had me discard the brushes I had been collecting and again recommended I make the investment in good quality ones and to be sure I set up a regular routine to clean them properly. Next they recommended I find a comfortable place for application and to set up a system that would help me organize the overall process instead of just throwing things into drawers. They did approve of the large vanity like area I had but recommended I fix the poor lighting it offered. I began to feel like some of the mystery was vanishing and I had some direction and a plan to go forward.

I had another friend install a strip of those globe lights above the mirror as he was much more skilled at this than I am and immediately saw the difference they made! Next it was off to the mall with my list, deciding it would be best to go mid week during the day when there would be less customers around. Yes I was nervous walking up to the counter, but the woman who was in her mid forties put me at ease almost immediately by taking the list and running back and forth behind the counter to gather samples. I am sure she thought I was going to be her windfall when she saw the list! Two hours later I walked out with several bags of products along with a list of tips she wrote down for me to practice. Walking back to the car I had the mixed emotions of elation and anxiety thinking can I do this? Can I make it all work and create the look that would give me confidence in all the different settings I would encounter?

I have to say it has taken a good deal of practice and I haven’t found many short cuts along the way, but it has also become something I enjoy. The advice and help has made such a difference for me and I am so glad I broke down and asked for it! For me, I focus on my eyes and after trying out different techniques I have found the ones I like and believe work best for me. I have learned how to emphasize what I want like my eyes while minimizing those areas like my nose. One of the neat things that has come out of this is I found someone I can now go to and count on her to continue to provide consultation advice along with resupplying me with the products I like. While I am spending a lot more now, the quality is so much better and I use less in most circumstances so I see this as worthwhile trade off and investment.

The next daunting task was to redo my wardrobe (oh I still kept a good deal of my going out for fun outfits!) and started by focusing on the right undergarments. Talk about a mystery! How does one figure out the mystery of finding the right bra size and cup size? I think I will save this for a follow on article. The main point I hope to make here is that it is possible to live your dream. Yes it takes a good deal of fortitude and commitment and you make mistakes along the way, but even the celebs do that if you ever watch the red carpet snippets!

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Diana A

An early 50's pre-op TS on her journey through life! I have a variety of interests I would love to share and hope to meet new friends here!

Latest posts by Diana A (see all)

  1. Darcy Bainsley 3 years ago

    Very nice. It’s always fun to have biological woman in your corner. It’s even more fun to have makeup consultants. My Lancôme ladies know what I like, what works, and help me in all the time. Not makeup related I know the manager and a couple of ladies at my local Layne Bryant store as well. Funny thing though is I’ve never shopped there dressed en femme. My next adventure is to go shopping there all dolled up.
    Thanks for sharing your thoughts and keep practicing.

    • Author
      Diana A 3 years ago

      Thank you Darcy! Isn’t it just awesome to have expert help? It has been making a world of difference for me!

  2. Great article Diana! Thanks for sharing your experience. I am hoping to soon make a trip for a makeover at Ulta or Sephora and learn more about the proper colors for me and application of makeup rather than the ad-hoc experimenting have been doing up to now. I look forward to reading more articles fro you in the future and wish you well in your continuing transition.


    • Author
      Diana A 3 years ago

      Thank you Cyn! I just know you will have an awesome experience when you go. I continue to learn so much about the fine art of doing one’s face so it has been a godsend to have someone to help with the advice.


  3. Terri 3 years ago

    I love going to the cosmetic counters. I like Estee Lauder. The sales people are always nice and have gotten some great makeovers there. A funny thing happened to me in Macys. I was buying a blouse and gave the sales girl my Macys credit card which has my male name on it. I was enfemme and she asked if I had been on America’s got Talent. She had mistaken me for a transgender comedienne contestant. I laughed and she was very nice.

  4. Janine 3 years ago

    Although I’m not going to transition I still enjoy dressing up as a female and have done the makeover in the stores that offer that service and have to say that I agree with you completely about how great it is to have a professional show me how to apply makeup so that it looks natural.
    It not only looks like I have had a professional do my makeup it doesn’t take as long to get the results that I’ve never been able to get.
    Like you I stressed about going to a makeup artist the first time but again like you I found that I was accepted and wasn’t embarrassed when I did it and asked for help with my makeup.
    I’ve gotten a lot of great advice and tips on how to apply makeup making it much easier for me to use and apply the right makeup for my features and skintone
    I urge everyone to do as what you and I did meaning take the step and ask for professional help with your makeup.
    It really makes a world of difference when you learn how to use and apply the right makeup
    .Thank you Diana A for your post.
    I know that it will enspire other cross dressers to try getting their makeup done professionally

  5. Leonara 3 years ago

    Diana A
    Thank you for relating your experience at the cosmetic counter… It gives a lady courage to get pointers from the professionals … I prefer Lancôme which my wife introduced to me. As my wife says practice.. Practice..
    Thanks again. Regards. Leonara to

  6. Charlotte Smith 3 years ago

    Hi, a great and interesting article with elements I can identify with. Not sure if i am allowed to mention commercial organisations but here in the UK I have at least found a [place to help me deal with the underwear issue! has all the correct information about measuring and getting a good fit for us girls.

    Hope it helps – love Charlotte

  7. Stephanie Cross 3 years ago

    Hello Diana A,
    Thank you for your article. Going to the experts for make up advice is one of the best things we can do. I had been collecting make up items that I thought would work for me. But then there was some confusion as to which part is used first and then what item can be used over another. So this got me no where and I’ve been out with out any make up each time. But this has changed as of Christmas Eve this year. My wife and I went to the MAC cosmetics counter at a Macys near me and I got a make over. They make it seem so easy to work with and the girls there had fun while helping. The one thing that will help me the most is the cheat sheet they made up for me to take home. My wife and I found out what items to use and in what order and what tool to use for each. We also tried to limit the number of steps needed to end up with the results we wanted. I don’t like having to spend a lot of time on make up like I see some doing. So now I need to practice and practice and make it work for the new and better look I can go out with. Thanks again and Happy New Year.

    • Author
      Diana A 3 years ago


      You go girlfriend! It is truly a game changer when you finally have the steps, tools, and right makeup all come together! I hope that 2017 will be an awesome year for both of you!


  8. Lara Cross 1 year ago

    Darcy–You are living proof for the importance of learning the basic skills to become a more beautiful lady. And when I consider that… isn’t that true for most things we attempt to do? Thanks for sharing. -Lara

  9. Anna Smith 10 months ago

    Hey there. I’m a beautiful woman trapped in a mans body, and I have no doubts about it. There’s not a passing hour that goes by that I dont urn to commit to embracing my inner beauty as a woman. Over the past few years, it’s gotten so strong that it hurts inside. A couple years ago, I started experimenting. I bought lingerie, makeup, nails,polishes, shoes,clothes, breast forms, and beautiful wigs. I would dress up all pretty, but feared going out. Something happened and I stopped. Just recently I have made up my mind to put in the hard work of becoming a woman, inside and out. World here I come!!

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