Do You Think I’m Pretty?

“The beauty of a woman must be seen from in her eyes, because that is the doorway to her heart, the place where love resides.”

~ Audrey Hepburn

I wonder often about beauty. I strive for a version of it every time I pull out my makeup case and prepare to transform into my Savannah persona. When I look in the mirror—after donning my wig and brushing it out—I question why I even bother to try. Sure, I am painted up. Sure, I managed to contour my cheekbones to be higher and my nose to be narrower. Sure, my hair frames my face in a much softer and more feminine way. I wonder if I ever achieve my goals of feminine beauty. The answer is difficult to know for sure. When I look at my features in the mirror, I still see my masculine jawline and wider nose. It is not that I do not notice the differences I affected with my makeup application. Ironically, I still see the face that I was born with and have seen every day of my life. It is not an easy thing to forget every line and curve of one’s face just because mascara and foundation have been added on top of it.

For a non-transitioning crossdresser like me, there is always the nagging question of how far to take our femininity—or how far can we take our femininity. There is only so much weight loss and toning to be achieved… only so much body hair manscaping to smooth our skin on a semi-permanent or permanent basis. Without hormones or T-blockers, we will not be redistributing our body fat to the chest, hips, or bottom. We will not lose muscle mass, or see our skin soften.

Beauty is always in the eye of the beholder
Beauty is always in the eye of the beholder

I point out these issues for a couple of reasons. First, we are slaves to the fact that we are men trying to emulate a feminine persona. Sometimes, it is an easy feat—sometimes not. Our image of what we should look like as a woman can seem a bit unattainable, even after our best efforts and hours of preparation. We think we haven’t succeeded, because we are still men underneath it all. We have an ideal of femininity in our heads that we may not be able to bring forth to our face and body without over-exaggerating it into a caricature. Secondly, social media—and glossy print publications before it—have set a sometimes-unattainable standard of feminine beauty. American cosmetic companies, smartphone photo filters, photo manipulation, and more have indoctrinated women from a very early age to strive for a specific level of beauty. The arches of our brows need to be shaped just so. Our skin needs to be smooth and soft. Our cheekbones need to be high—and pop. A social standard of the feminine ideal has been set and has been set for many years, defining something that is both beautiful and unrealistic.

How do we reconcile the practicality of our masculine identity and physicality with that of what we strive for in our feminine version? Sacrificing our birth biology to supplement our need to express the opposite gender once in a while is not an option. That being said, we do wish the transformation was simpler. Why do I have to add breast forms? Why is it imperative to have padding for our hips and bottom, while whittling down the waist to the point of pain and the difficulty to breathe? Why are the 38-34-36 proportions so important to our presentation?

One is indoctrinated with certain criteria for what is considered the standard of beauty, whether corporately or culturally. Can I be considered beautiful if I have broad shoulders and dark hair on my forearms? What if I still have a bit of paunch on my belly that cannot be melted away with layers of Spanx or laced-up corsetry? The answer is simple… Yes. The old cliché, “Beauty is in the eye of the beholder,” holds true for me. There is beauty in everyone—enhanced by the heart and spirit; magnified by the person’s self-confidence. Real beauty is as individualized as sand on the beach. There is no absolute standard. In fact, its definition is always in flux.

I struggle with how well I achieve my look as Savannah. I struggle with the belief that I possess feminine beauty in any degree, measured by current social standards regardless of the compliments I may receive. This deficiency in self-esteem is something I continue to work on for myself. I know others see me in a way less critical and more complimentary than how I see myself. Many—when I show them a photo of Savannah—can’t believe that she is actually me. The concept is a difficult reality to understand when all I see is the male me. I always see beauty in the people all around me. I just need to remind myself they also see beauty in me—in whatever form they find flattering.



Author: livingwithcrossdressing

I am many things. I am a life-long male-to-female crossdresser and author. I hope my journey is of value for those who may need help to foster, support, and understand who they feel themselves to be.

One thought

  1. Beauty is in the eyes of the beholder, and when I look in the mirror wearing a different wig, I see myself differently. I’ve been cross dressing twenty four years. I am sixty nine years old, my wife passed away recently, and I’ve given my self permission to fully explore my femininity. At my current matronly age, the bar for ‘passing’ is much lower, but I say ‘Better late than never!’ I spent a weekend wearing press on nails, and like them, but it also felt like a form of crippling adornment, limiting my dexterity. I understand why the Japanese used to bind their womens feet. I’m wearing more gender neutral clothing in public, to minimize my male presentation, except when I have to work. I recently got my ears pierced, and I am wearing earrings. I am growing my hair out, so I can have it styled to look more feminine. I am seriously considering getting a butterfly ‘tramp stamp’ tattoo just because…

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