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Well, a lot of it was simply practice. I've been playing with it since I was 15, and most times all I would do is just put it on and try different looks. By doing that I learned what eye shadow and lipstick colors worked for me and which ones didn't. I learned how to apply the right amount of blush to my cheekbones without looking like a cartoon character.
I paid closer attention to how biowomen who wore makeup looked while they were out and about in the world. I emulated the women (and my transgender sisters in Montrose) whose looks I liked and used as cautionary tales the looks I didn't like. (using black eyeliner pencil to line lips, for example)
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That was difficult for me because in junior high I got hit in the left eye with a balled up piece of pottery clay in my 7th grade art class. I still have a reflexive motion as a result of that incident that causes my left eyelid to rapidly shut and water anytime some foreign object gets near it.
The involuntary eye shutting reflex caused me major problems during baseball season the following spring because for a right handed hitter, you are using your left eye to spot the ball. For most of the early part of that season, anytime a pitcher threw me a curve ball, my eye and brain perceived it as a 'Danger' moment, the eyelid fluttered shut and I missed badly while swinging at the pitch.
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I fought to get over the shame and guilt of actually walking up to the makeup counter and buying what I needed for my forays into Montrose. In addition to that, I went through a trial and error period before I finally hit upon the right combination of products that work for this Phenomenal Transwoman.
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I'm a firm believer that you can learn something about any subject from reading books, and makeup application wasn't any different. As a matter of fact, two books that had (and still do) occupy prominent places on my bookshelf are Sam Fine's Fine Beauty and Reggie Wells' Face Painting.
They are both renowned celebrity makeup artists who dealt predominately with African-American celebrities. Reggie Wells was Oprah's Emmy Award winning makeup artist while Sam Fine was Tyra's and a few other sistah supermodels makeup man of choice during the 90's.
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To emphasize that point, she took a photo of herself without makeup and highlighted all her imperfections, then showed a picture of her with makeup on.
The book's message was something I already knew before I transitioned, but it bears repeating. It's what's going on inside personality wise that makes you beautiful.
But the makeup tips was what i bought the books for, and I surmised if I was going to learn the basics, short of getting help from a biowoman about it, what better teachers than those two men and a supermodel?
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I finally decided to try the two makeup giants for African-American women at the time I transitioned, Flori Roberts and Fashion Fair. I started with the Flori Roberts because it was slightly less expensive than the Fashion Fair, and struck paydirt with a cream foundation shade that matched my skin tone perfectly. For several years I bought it until Flori Roberts counters started disappearing from department store makeup areas in the wake of the department store merger and acquisition wave of the 80's and 90's.
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I use Coty's airspun loose translucent powder that I get from any drugstore, and it's the same place I get my pencils, my lip gloss and my Maybelline mascara. I only do mascara if I'm going out since I have naturally long eyelashes already.
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If you're a t-sistah on a budget, Posner's still out there along with the Cover Girl Queen line. Haven't tried any of their stuff yet to see if there's a shade hat works for me just in case they run out of my fave Fashion Fair one. It seems like half of Louisville wears my shade, and I have to make sure I have a backup when Derby and Christmas are approaching.
Oh yeah budding t-girls, don't forget that if you put it on, you have to take it off as well. I'm blessed with smooth even toned skin and I take care of it. I'm armed with facial cleansers, soaps, astringents, and facial masques to make sure I get whatever residual makeup is on my face off of it.
On that note, it's time for me to do my facial. Later peeps.