Leather or Leggings

Although living full-time or transitioning is not for me, I do wonder what my style would be if I did. When Hannah struts out of my boy life, she is alllll about dressing to kill. False eyelashes, bold makeup, heels, cute dress, and a tightly cinched corset. I feel amazing.

But if I am being honest, it does feel nice after a day en femme to undo everything and put on clothes that, well, require less maintenance.

I have a lot of thoughts when I get ready and alllll of them are superficial. Hoping that I look cute, hoping that my dress shows off my legs, hoping I can manage all day in *these* heels. I plan my outfit but I also plan on HOW I will put it on. For example, my corset limits my movement a bit. Not very much mind you, but if I am wearing heels that require me to bend over or kneel in order for me to fasten them, then I make sure I put my heels on before my corset.

Since it takes me about 30-45 to shave everything and everywhere, and about the same time to pick out an outfit and get dressed and even more time on top of that if I am doing my own makeup, I often think that I’m glad I don’t have to do *this* everyday.

Don’t get me wrong, I love presenting en femme. I love every second of it. I love wearing my corset and stockings and eyeliner and stilettos. Love it.

But again, it’s a lot of work. I do LOVE the work and I do LOVE the result, but it is a process.

It’s pretty clear that Hannah is pretty *extra*. I would never, ever, EVER say she’s the prettiest, most femme girl at the mall, but she is usually one of the few wearing heels and a dress.

Most cis gender women I know very rarely wear a dress or heels or makeup beyond foundation, subtle lipstick and a touch of mascara. This is not a criticism AT ALL. This is also NOT a competition. Every girl should wear whatever the hell they want, whether that is five inch stilettos or zero makeup. That’s the fun of being a girl, doing whatever you want.

Some crossdressers tell me that they don’t understand why a girl doesn’t wear a dress or heels everyday, especially since they are “allowed”. I… I get it, on some level. I mean, dresses and heels and super fun to wear and I dress to the nines when I do have a chance to dress.

Every woman (trans or cis) has a different experience when it comes to preparing for the day, but for me, getting ready takes a lot of time and effort and money. If I wore foundation every day, it would get expensive since the type I use is pricey. After twelve hours in heels or after an expensive shopping trip to Sephora, I am, on some level, glad I am not en femme every day. Mind you, I am not saying that presenting femme does NOT necessarily mean heels and makeup. I heart a tight leather dress, but I also heart relaxing in leggings.

I do wonder what my look would be if I was full-time. Would I wake up each morning and wear a dress? What would I wear if I was feeling a little lazy? What would I wear if I was spending the day running errands? Would I have bold eyeliner and false eyelashes all the time? Would I wear my corset each and every day?

I can’t imagine doing that. But of course at the same time, I can’t imagine leaving the house in flats.

There’s also the emotional part of getting ready. As I begin “the process” I am trying as hard as I possibly can to turn *this* into who I hope is a pretty girl. If I am having an ugly day or my dress isn’t as cute as I want it to be or my makeup just isn’t cooperating, it can really ruin my day and destroy my confidence.

This is not a critique on any girl that chooses flip-flops over thigh-high platform boots. I get it. If I was full-time I am sure that I would have shoes that aren’t heels. I’m sure I would *shudder* wear pants. There would be days when I would opt for a light makeup look.

For those of you who have made the leap (or strut) to full-time or transitioning, how has YOUR look changed?

Love, Hannah

3 thoughts on “Leather or Leggings

  1. Well it is like anything else, learning what works and what doesn’t, and what you feel comfortable wearing. I started transitioning 16 years ago, and living full-time almost as long, as special as I would like to think I was at the beginning, I can unequivocally say that I made the same damn mistakes all girls (cis or trans) when we start out, we try to be too girly (or womanly).

    Part of it was the new, the unleashed spirit, all the things you dreamed about as a crossdresser that you now have free range to do as a girl. Another part was overcompensating, from one extreme to the other–though you would never have confused me for being too masculine when I was male, maybe preppy. I dyed my hair different colors and done in different styles, I got all different types of fake nails, I wore too much makeup or the wrong makeup, undergarments uncomfortable and retraining, wore dresses and the wrong heels all the time. The latter was quite impressive, considering that I have big and wide feet with high arches, though, I live in an area with casinos and strip clubs, so showgirl/stripper heels of various sizes are in abundance.

    But you can’t wear stripper heels all the time, makeup-wise you can’t be glam all the time, corsets are not practical every single day (though some curve management is needed), and you can’t be in dresses that, let’s just say are quite revealing all the time. I actually had a supervisor say: “I don’t want you wearing something that shows your boobies. It’s not appropriate.” Added to that, there’s weather considerations, and I had to learn that one the hard way. I had a pair of heels melt from the extreme heat from pavement in the summer, and I caught pneumonia from not wearing enough layers in winter that same year.

    Once the mistakes out of the way, then the real learning comes into play. What you feel comfortable wearing. How much effort and energy you want to put into a look or not. And yes, how you feel that day.

    My friends call me the girly-girl of the group, since most days I wear a skirt and a top coupled with a cardigan or a coat. (What can I say, I like looking cute.) Dresses are either for special or summer heat, I have both, and shaper wear underneath (for what, it is none of your damn business). I never got to a place where I felt comfortable wearing pants as daily attire, though, I do wear yoga pants for the gym, yoga, walks, and lazy Sundays. I do wear makeup daily, but it is more like the TV version of a girl waking up–light foundation, powder, lipstick, eyeshadow, and mascara. If it a special occasion, a night on the town, or I just want to feel pretty that, I put little more effort. As for shoes, I still wear heels, just not the platform stripper variety. I switch between pumps, booties, boots, and sneakers (flats hurt my arches).

    I won’t say there weren’t other stumbling blocks along the way (bathroom politics was/is a touchy one), and they don’t still exist today (my voice the other touchy one), but in the end it all comes down to what feels comfortable on the inside and outside.

    What you’re daily look would be? Well you would forget that out for yourself.


  2. Hi Hannah and everyone. This post brings up a lot for me. I’m 65 now and started my transition at 60, in mid-2017. Wow, such a rollercoaster of emotions and all that but so much happier and grounded than I’ve ever been before.

    At first I assumed I needed to “act my age” and wear more conservative grand-motherly clothes but they looked so uninteresting and boring to me. A cis girlfriend advised that as a woman I could wear anything; all was okay.

    I bought a lot of clothes. Everything from more formal dresses to skinny jeans, blouses, shirts, tights, leggings, you name it. I was fortunate to make close friends with several cis lesbians by joining them on hikes, pot luck dinners, camping, and we talked about everything. In all of our get togethers I was the one who dressed up, just a bit. One friend used to tease me that I was their “fashion plate.” Over time, another close friend advised that I didn’t need to look so feminine. She’s not butch by any means; I think she was calling my attention to how I kind of stood out relative to the rest of the women, not only in our group but also just doing things like shopping for groceries. I started looking more closely at the women around me and sure, they didn’t dress up so much. But I also understood why my previous girlfriends (and two ex-wives) loved dressing up for more formal occasions.

    I’ve found that my style is more what we called “California casual” (when I lived there). Often skinny jeans, appropriate shoes, a nice top, and maybe some jewelry. (always some simple earrings.) I don’t wear makeup. Sometimes some lipstick, and sometimes some perfume.

    So, I’m just like any other woman out there, just going about her life. I used to think that I am a trans-woman but of late I’ve realized that I’m first and foremost a woman, who has a list of other characteristics including things like: I used to be brunette, I was born/raised in CA, my dress size is mostly 14 (although I strive for 12), and oh yeah, I’m trans.

    I think it’s cool that Hannah dresses to the nines every time she gets ready to go out. When I did that early on a pair of lesbians (who’re married) told me once with a chuckle that neither of them even owned a dress. I thought about it for a moment and replied that it just felt so good for me to do so, something that had been forbidden fruit. They were cool with that.

    Yesterday at an electrolysis session (almost done, thankfully) my electrologist who’s a mid-30s trans woman joked that she’d thought about adding electrolysis to her dominatrix “punishments.” (Yes, she does that too.) As I laid there I thought back to my dreams and fantasies about being coerced into feminine clothing (French Maid, anyone?) and realized that I simply don’t have such dreams any longer. I have the luxury of just… being me.


  3. Though a new-comer to being full-time – less than a year, I’ve been moving in that direction for ages and ages. And with that, I’ve definitely shifted towards the “blending in” mode of appearance. I’ll still wear skirts or dresses, but usually it’s when I’m going to be going out. And not every time even then.

    Leggings, jeans (of various styles), and slacks all play into daily choices. I’ve become fond of a top and a cardigan, though I can’t wait for the warmer weather to not have to layer so much.

    Tenners or a low wedge most of the time, but I have found a cute pair of ankle boots with a heel that have been paired with most of the above outfits. Another item waiting for the warmer weather are my ballet flats. Oh, and bare legs in the warmth.

    The “$100 makeup” has been mostly replaced with tinted moisturizer, mascara, lipstick, and maybe some shadow. If I’m getting made up at all – I’ve been out to events lately with just mascara.

    And, I feel great about it. I don’t feel cornered into a narrow set of looks. I can choose between a huge variety of options. I can vary my choices based on what I plan to do, where I’ll be, who will be there, etc. It’s opened the closet so wide, it’s amazing. My three plus hours to get ready has been replaced by getting ready and out the door in minutes at times, and usually well under an hour for “the works”.

    I am working on plans for outfits for a few events coming up – I’ll be in the office a couple of times this month, so that’s going to be a new set of things to think about. And then April 1 and 2 I’ll be representing the company at a booth in the Mall of America at the Fan Fest for the Women’s Final Four and the 50th anniversary of Title IX. Definitely a new set of challenges to think about there. And maybe some shopping. 🙂

    And yes, there are still days where “I don’t have a thing to wear”. 🙂


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