Crossdressers Dressing for Success

As part of our Sister/Cis-ter crossdressing conversations—in an effort to better understand the male-to-female crossdressers’ mind and purpose—Savannah Hauk, author of the “Living with Crossdressing” book series will enjoy ongoing discussions with Julie Rubenstein, a certified image consultant and co-owner of Fox and Hanger. We will delve into our personal battles and experiences, all with an eye to enlighten and entertain our beloved crossdressers and our supportive allies.

If I hadn’t been a woman, I’d be a drag queen for sure. I like all that flair and I’d be dressing up in them high heels and putting on the big hair. I’d be like Ru Paul.

Dolly Parton

JULIE

Ah. I just got dressed. What a game changer. Wearing bright colors and my favorite earrings.

SAVANNAH

Still love those earrings

JULIE

When I discovered these, or when I find any faux ear stretch angel /swan wings, I know I had found something that reflected my authenticity. Gracefulness mixed with edge. I love pairing with non-edgy clothes. The dichotomy excites me, and I love the fact I can pull off ear stretchers. Nobody knows they are fake unless I tell them, which I always do! I have a tremendous amount of confidence when it comes to the art of self-expression.

Do you have anything you wear that, once you put it on, you’re like, “I’m home”? Maybe, it’s not as simple as a specific dress or a pair of heels. Like life, it can be more complex than that. Perhaps It isn’t one thing at all, but rather a series of ingredients helping the return home. During a pandemic, it can be so easy to lose yourself… unless you put in a real effort.

SAVANNAH

My feeling of completeness and peace is really rooted in having moments to express myself as Savannah. I will say that I would rather wear a dress than jeggings, a blouse rather a shirt… the more feminine the better. The feel and stretch of the material is very important, too. Am I a fashionista? Not really, but I think I manage to coordinate my outfits well enough with a sensible-enough fashion palette (in my own eyes). So, like many crossdressing men, I am grounded and rooted to the earth when I wear sexy or satiny panties and other intimate garments. That is the foundation, no pun intended, to be enveloped by padding, breastforms, and bodycon dresses. It’s the attention to detail with the makeup, the swoop of the locks of the wig, and one of my Phoenix necklaces that make Savannah feel complete. Wrap that all up with being out in the world… being with my friends or being visible… those ingredients combine together to feel real and home.

JULIE

That’s beautiful.

Your words paint a picture of a multi-sensory experience, with an attention to detail paired with a deep understanding of your needs. I appreciated what you said about feeling “grounded and rooted to the earth” when you wear panties and undergarments. So beautifully said! I have that same feeling when I wear hats.

Did you know I don’t own something sexy like a corset or some eff-me heels!? I feel like as sexual as my energy (and humor) can be, owning sexually-overt clothing could be too overstimulating. I might take it too far and start humping trees in a thong and corset. Or, perhaps I will start humping everything in sight and change my name to Tabitha! I would be as grounded as an astronaut in space! As a cis-woman, I have such an appreciation for the male-to-female transformation. This appreciation began when I was nine years old and saw Divine as Edna Turnblad in Johnathan Waters’ Hairspray. Currently, my work with male-to-female individuals has given me a small window into this beautiful process. Thank you for describing your creative process when “becoming” Savannah. I hope to someday walk beside you, just us girls. I may actually wear underwear that day!

SAVANNAH

Ironically, your comment about feeling overstimulated if wearing a thong and corset is somewhat what many crossdressers feel in a real way. Some men wear lingerie, bra/panties sets, and pantyhose strictly to feel that over-sensualization or -sexualization in their feminized form. If they discovered their crossdressing during adolescence and started equates their dressing with self-pleasure, it could become a self-fulfilling cycle of dressing = pleasure.

There is such a fine line between our gender expression and our sexuality. In some ways, they are so very intrinsically connected and feed off each other and, in other ways, they are mutually exclusive concepts.

There is a nexus—a crossroads—where we should give ourselves permission to feel all the sensations and feelings converge. We cannot, and should not, divorce the sensuality and soft femininity of our presentation from its emotional context. Can we be expected to see the satiny lingerie on our feminized bodies in the full-length mirror, feel the material through our fingers and the tightness of the articles against our bodies, and practically experience this—up to now—forbidden expression without letting our raw emotions and true gender identities mix and mingle for a totally surrendered sensory and psychological moment?

JULIE

There IS a fine line between gender identity and our sexuality. I agree with everything you are saying. Yes, I think that the two can be mutually exclusive. But, it must be really hard—and really confusing—for crossdressers who haven’t experienced their femininity during adolescence and keep on trying to kill off that side of themselves. With all the available information and all the ways to identify one’s gender and sexuality, it can be overwhelming and really confusing. I have met individuals that have a desperate need for a box, or a diagnosis, or an answer rather than the freedom to explore and express. If they get turned on… well then, let’s just call it a kink? If they feel grounded and at peace… well, trans it must be! But, is that right?

I know I have told you this before, thank you, God, for your book, “Living with Crossdressing: Defining a New Normal”! Seriously, if I was a crossdressing male, that book would be my lifeline. As an ally, it was that one missing piece I needed to fully understand all of the complexities. Without the information (ie: your book, this blog), everyone is just lost. To think that so many male crossdressers have gone to extreme measures because they decided that they must be transsexual… when it was just a lack of information and support.

Oh, the agony I feel over this is endless! This painful reality aside, I believe that in order to fully comprehend and embrace the complexities of one’s femininity, there is a part that must be surrendered. Lovingly send that part of the brain packing. There is no need for an eraser, a box, or a timer to “figure it all out”. There is a softening and the creation of a safe space for your feminine side to find its way to. I like when you touched on emotions and allowing ones “true gender identities mix and mingle for a totally surrendered sensory and psychological moment.” THIS IS SO IMPORTANT!

There are endless tools and opportunities to awaken your femininity that go beyond “looking like a woman”. Some of the individuals I work with have found comfort in putting on a pair of high heels and simply tuning into how their insides feel and how easily they are able to activate feminine movement. What about smell? To purchase a scented lotion or hand soap. A feminine scent has a really intense way of activating one’s feminine side. What about your sight? To noticing how women move in the world is an important practice. Observing the differences between men and women. How woman don’t take up as much space when they walk. Noticing women’s posture. Practice in the mirror. Practice at home. Practice in the world. And, don’t get me started on touch! Let’s just say we are sensory beings. And, all this can be extremely arousing for a novice (or, an expert). I can especially empathize with the sensual pleasures that come with the sensory experience. One of the reasons why I started styling people virtually is because clothing turns me on! I was Nordstrom Rack with a client and I literally let out an orgasmic moan, as I slid my hands down an entire rack of Free People clothes (and, OH YASsssss, everything was 40 percent off!).

SAVANNAH

All of the senses are critical in finding your “trueness“. Some love the smell of perfumes as a final touch while some love to lather up with the flowery scent as they bathe or shower beforehand. Yes, watching women move around in public to see how they comport themselves is also a key component of how to become more feminine. They do draw back their shoulders back, keep their arms closer to their bodies, and walk in a straight line with a more swaying gait as they walk with one foot slightly crossing over the other. They glide across a room… not lumber. When they sit, they exert a straighter posture and cross their legs at the ankles or press their thighs together. Of course, this is not true of all women, just as masculine traits are not absolutes for the male of the species.

JULIE

Exactly.

SAVANNAH

Our conversation delved into what artifact or totem empowers us or grounds us—or both. Clothing does have power… an inherent power. The fact that dual gender men find their femininity in soft and silky designed-for-female fashion is a testament to that. A woman who comes home from the office, unhooks her bra, pulls off her heels, and peels off her pantyhose in favor of yoga pants and a comfy T finds solace and calm in those casual clothes. They represent the exchange of work and stress for relaxation and escape.

JULIE

I agree and have a deeper understanding on what it must be like to be a cross dresser. So, thank you for that. Clothing does have power. When I think of that power, I see it in terms of energy. Both the energy that comes from the people wearing the clothes, as well as how they are world received in the world. The energetic shift, when someone slips into something, has a frequency. Especially, if the clothing represents a change in scene in your life. Thus, a change in energy. When stepping out into the world, I always recommend that people wear clothes that make them feel happy, joyful, and grounded. When entering the outside world, one must find a way to present in a way that is appropriate. Because people lack information, we make assumptions based on outward presentations. We just do. What you wear sends an important message about who you are and what’s important to you.

SAVANNAH

I definitely agree that clothing changes how we feel and how we see ourselves. There is some push/pull in terms of appropriateness versus individuality. Crossdressing men may be “clocked” when dressing in something others may consider inappropriate, but it is less about public opinion and more about the individuals happiness in how they present themselves. In order to be most authentic, it is important to remember one’s self. I am not saying that somebody should wear thigh high boots and glitter to Starbucks, but I am seeing that style is just as important as situation.

JULIE

Yes!!! One must remember one’s authentic self, which takes some practice and investigation. Depending on your personal style esthetic, there are ways to tap into that without compromising your safety or individuality. Finding your authentic style is a hard for most people. But, for crossdressers, it is a part of your identity as a woman in the world. When you able to dress in something that brings you joy… ooh, honey, watch out! What would it be like to live in a world where one could exist without barriers. A person could rock a pleather cat suit and a hamburger purse, a kimono, or a ball gown, and it would be as supermarket appropriate as a pantsuit. Now, I may be speaking about a comic book world or the book I’d like to write some day…. The way we choose to express ourselves is both a divine right and a compromise.

SAVANNAH

Exactly. But, does it need to be a compromise?

JULIE

Well, I believe it is a choice. But, especially for transgender women and crossdressers, I believe that the stakes are much higher. But perhaps that’s their truth, to go out in what feels like them and fuck what anyone thinks! Now, this is an empowering stand. As an ally, I am extremely protective. If I had a magic wand that could make this world a safer and more accepting place I would. And, that is why helping crossdressing men feel empowered and confident enough to step out in something that captures their authentic spirit without putting them at risk (or a target) is important. Do I want them to be a sheep if they are a lion… NO! But, I do think it’s important to dress for the occasion.

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