Close this search box.

This Week’s Advice: Get a Makeover

More Great A-Dee-Vice!


My suggestions so you can Dee-It-Yourself for a better and a happier life

After writing about finding happiness, one sure fire way for me is having a makeover. Over the last seven years, I’ve had three, none since the pandemic. I am overdue.

They are fun, but more importantly, if you pay attention and buy the products, I believe you can Dee-finitely up your makeup game. It worked for me.

In October 2016 I had my first real stab at going out regularly. My second step (the first was getting my fingernails done) was having a makeover at the Sephora at the St. Louis Galleria. I chose Sephora because one time I was walking with my wife and her best friend and my wife recommended Sephora, and that stuck with me. I had also read that Sephora was (and I have found out, are) very TG friendly. 

Five days before I wanted to have the makeover, I screwed up my courage and went into the store (as a guy) and asked to schedule a makeover. The staffer–a guy, by the way–said sure. I asked for a less popular time, and he suggested 2:30 PM. 

Note: that was a mistake, as I found out. I should have done it first thing in the morning, so I would be able to enjoy it all day. I almost cried when I had to remove the makeup that night.

Julie, my MUA–makeup artist–was absolutely fabulous. She would look at my face, ponder for a while, then go to work. She would explain the technique, and the product, and I borrowed some paper and pen and literally took notes of what she did and in what order. I still have the notes, but I’ve done it 500+ times since then, so I have memorized the process. I also bought a lot of the products (warning, not cheap, but worth it to me), but having the lesson and products gave me an immense sense of confidence I could do a reasonable job of doing my own makeup.

Since then, I have generally simplified things. I rarely do my eyes, which saves time. I would love to be able to do a cateye or the like, but I can’t, and I don’t get enough practice to EVER be any good. Plus, I rationalize I wear glasses and people can’t see eye shadow anyway, and if someone is close enough to see my eye makeup, they are probably a friend or someone who can figure out I’m on the TG spectrum. I have found that less is better; easier to put on, easier to take off (which is often a significant consideration for some of us, including me).

The most important thing is to get the right foundation and powder to make sure the canvass is right. For me, my beard is pretty light (called older age), so I don’t have a real issue with beard shadows. After that, brows, some mascara, blush, a little pencil around the eyes–and then try not to mess up the lipstick. 

And by all means, if you go, go dressed. While I know the idea of walking into a place without makeup while dressed is daunting (it was for me), you will definitely kick yourself having a pretty face–and then having to swipe it all off before you leave the store.

There are tons of places that do makeovers like Ulta, MAC, Merle Norman, all of the major department stores (Nordstrom, Macy’s, etc al), so lots of choices. You can either call them or visit before and ask about scheduling a makeover and thereby judge how enthusiastic they are with dealing with a TG person (likely they are, because they tend to love makeup and love even more having paying customers). Usually there is a minimum charge for the makeover, but you will most likely spend a lot more than the minimum in product.

Now that Covid restrictions are mostly past, do yourself a favor and schedule a makeover….and then come back and thank me for suggesting it!

Shop some of the top seller’s at Amazon!


4 Responses

  1. Great post, Dee.

    I’d like to add my endorsement to this. A makeover can be a truly transformative experience, particularly for those who have been deeply closeted up to that point. There’s the experience itself of course but it also demonstrates what is achievable; we have to be realistic about our own skills and abilities to replicate the work of the professionals but it does give something to strive for in our own endeavours.

    And then there’s the interaction with the MUA. Being able to talk to someone who is non-judgemental and encouraging of this side of us is cathartic and, whilst my experience was in a dressing service, I can honestly say that a very different person emerged than went in four hours earlier.

    This should be on the bucket list of every CDer!

  2. Great advice, Dee! And a new idea, thank you!

    I have been able to find M-T-F makeover/makeup artists many times while traveling: Philadelphia, Tampa, San Francisco, San Jose, Los Angeles and Nashville. Each experience – many of which you can see on my Flickr pages – was amazing and made all the difference in the world. Especially, as you say, if you going “out”.

    The idea of make an appointment at a retail makeup counter had not occurred to me, so thanks for that.

    Interestingly, since I opened up to my wife about Crystal, she has “hinted” that she would like to try doing my makeup. I don’t want to press and I am sure it will happen at some point. Now I am thinking of taking her with me to the makeup counter, so she can learn any new techniques and better understand “my” face!

    Cheers my Friend,

  3. Dee,
    I do feel it’s important to get professional guidance , we have choices where we find that help . Some love the day of total pampering followed by a selection of photographs , this can be an expensive route especially if it’s only allowed to exist for a few hours . I took the other route , I knew I would shortly be attempting to go fulltime , up to that point my makeup had been odds and ends passed down from my ex-wife and daughter so I didn’t really know what was right for me . One rainy Sunday morning I dropped into a shopping complex and asked a superviser in Boots if I could have a skin colour test ( yes I was in male mode ) , she asked me to wait while she found a beautician , I was then taken to a booth but still in full view of passing customers . She was great assessing my colour with the scanner to find suitable colour match , at first she said she would apply spot tests but instead worked on the whole left side of my face . she was very grateful because it was the first time she’d worked on a male subject . While I could see customers stopping for a second look I didn’t care because I was taking it all in and asking questions . Finally she cleaned me up and then acted as a personal shopper taking me round the various brands advising me on the choices . It was a wonderful day , it gave me so much confidence knowing I had the right items and more importantly how to apply it .

    Now after 5 years I don’t give it a second thought , after showering and shaving I always apply light makeup , I agree it’s not how much you apply but how little to achieve the right result . If I’m only about the house I normally don’t apply blusher and finishing powder which is fine as someone is always ringing my doorbell .

  4. Hi Dee,
    Excellent post and I totally agree with you. I was going to a dinner party in Vancouver which was about a 3 1/2 hour drive from where I live. I arranged my appointment for 3 hours before the dinner party. So I had to drive all the way with no make up.fortunately it was sunny so with lipstick on and sun glasses on I made it through the drive through with out getting weird looks.

    It was done at Shaivona’s salon in Surrey. She is a member of a CD group I joined, Gurls in the Burbs, and she does make to female make up. We really hit it off together so once she was done she took a bunch of pictures of me as well as a video of me. She did a wonderful job and the pics I posted got a lot of compliments.

    Trish ❤️

Leave a Reply

Your email address will not be published. Required fields are marked *

Featured Posts

Get The Latest Updates

Subscribe To Our Newsletter

Sign up for the first look at Kandi’s outfits, blog posts, and product recommendations.

Keep Reading

More From Dee