Perhaps this post is a little late in the year, but its main idea can be applied to any time of the year as far as crossdressing is concerned. Like many, when I really started improving my dressing, I longed for a pair of high heels. There is just something about these shoes that presents such an air of grandeur.
When I finally got my first pair a couple of years ago, I was ecstatic! This excitement culminated with my first time strutting around the apartment wearing this newly acquired footwear but gradually dwindled as my feet began to hurt. The initial awe was further deflated as I realized how very difficult it is to walk in high heels.
Adding to my now fading happiness was the fact that most of the gorgeous shoes for women from the best brands stop at either size 11 or 12. So, with pain on the mind, the prospect of relearning a basic activity (walking), and the scarcity of cute shoes, what’s a t-girl to do?
To my surprise and delight, the answer came from my habit of people watching — I usually observe what females my age are wearing in order to get some fashion inspiration. What I noted was astounding, and can certainly fly under the radar if you’re not paying attention.
(Most) young women wear flip-flops! Once I realized this, it befuddled me that I didn’t see it before. Of course, warm weather plays a large factor and I had recently survived a brutal Chicago winter — but once the weather improved, there it was. On a daily basis, either going to class or scuttling off to the grocery store, females all around me were ditching the heels and wedges for the simplicity of a flip-flop.
Now don’t get me wrong, I’m not demonizing high heels 
, as they are still among my favorite fashion pieces. I just want to twist your perspective for a moment and get you thinking in a way you may not have before.
Sure, when it comes to special events and evenings out, many women are going to slip on some great looking shoes even if they make their feet feel like they are being squeezed in a vice grip. However, I think you’d be surprised to learn that even genetic girls struggle with walking in heels.
During my college graduation, I vividly recall seeing a gorgeous young lady in full regalia, making her way to the arena where the ceremony was being held. As I observed her, I noticed something very strange — she wasn’t walking gracefully but rather like she had been drinking — a lot. Of course she hadn’t, it was just that she had little experience walking in heels.
I smiled brightly as she gripped the guy she was walking with to maintain some sort of distorted balance, and at the same time felt a bit relieved. Because this girl who appeared to have it all together (appearance wise) could barely make her way across the parking lot, I understood something that would help me in my own journey.
Though the lesson wasn’t completely learned that day, over time I’ve discovered that being a MTF transgendered person doesn’t have to involve memorizing new mannerisms and relearning basic motor skills. If you choose to walk, talk or gesture in a more feminine way then more power to you, and I say go for what makes your life more enjoyable. For my part, there are definitely some aspects of femininity (as I perceive it) that I really gravitate toward and aspire to emulate.
However, please always remember that you should do what is right for you. Many of you have communicated these same feelings with me either via comments or e-mails and I applaud you for being true to yourselves. Being feminine can mean so many different things and is almost always in stark contrast to the typical male depiction of what it should be.
Keeping this in mind, wear what you want, walk how you want and talk how you want, but don’t do it because you think it’s required, do it because it makes you happy. Now get out there and strut your stuff, whether it be in a 5″ stiletto or a boring pair of black flip-flops (like the ones I wore at Be-All 
)
photo credit: Quinn Dombrowski
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{ 33 comments… read them below or add one }
I think there is a tenancy to over compensate and act too fem which will get you more outed being natural is often the best policy.
Very true, natural is better
Thanks, girlfriend, for a very liberating post. After buying so many pairs of heels, I nearly freaked when I discovered flats. Duh! You know what? It makes so much more sense to learn to dress from women than it does to learn from T-girls! I’m so gonna buy some flip flops in the spring!
You’re very welcome Teena, thanks for the comment. Heels are awesome, but flats are more practical in certain situations.
Coupled with skinny jeans or capris, I wear cute flip-flops a good two thirds of the time. With the amount of walking I do, it’s a matter of prudence and I hate the pain that heels cause. Still, sandals coupled with a small heel can look devilishly cute too!
Great point, Lori, flip flops don’t have to be boring, there are so many gorgeous styles out there.
Ohhh .. I can’t relate to this!
Although we do all have our own concept of femininity .. a good thing .. and it’s very cool that some are into the flip flop look, I find it quite destructive to the illusion many of us are trying to maintain.
Walking in heels is something that can easily be learned if the desire is truly there.
There are two things many of us try to hide. Hand size and feet size. It’s even a problem for most post-ops because neither are correctable, even by surgery.
From an appearance point of view, the perceived size of our feet is directly related to the amount of real estate they occupy and the toe-to-heel distance decreases with heel height. Also, in flats, we tend to return to that “male walk”. Yuk!
I’m not trying to rain on anyone’s parade. As Jessica mentioned, we all should do what’s right for us but I’m sticking with heels, and tend to pick the venues where they’re appropriate. Jeans and 4″ heels are appropriate casual wear, in my opinion. No beach for me!
Of course, your mileage may vary.
For sure, learning to walk in heels is on my to-do list
, and when I find a cute pair that fits me, I love the way they make my feet look.
Jessica, I was closeted (read- “in house”) for most of my life. As I got out although I love my heels, they were not always practical. Like in my first trip to the mall!
I do have some lower heels, maybe 2″ or so and they are ok, can keep the walk, but I have been looking for the right flats or just sneakers. Comfort and blending.
I am in Chicago now for a couple of days, what do you recommend for a night out? Remember, its raining.
Ellen
Lower a.k.a. “kitty” heels are much easier to walk in and still look fabulous. I absolutely love femme looking sneakers and have been trying to get my hands on a pair lately.
In Chicago, the area known as Boystown in Lakeview has a couple of trans friendly places. I’ve never been to any, so I wouldn’t feel right recommending any of the places, but have fun in The Windy City
!
Hehe I hear ya girl. I actually bought some cute green flipflops a while back and I wear them in guy mode too lol.
When I first started dressing, I was all about heels only and dresses/skirts only too. It’s funny though because now I’m totally ok with flats…there are tons of cute ones! And flipflops included. Same goes with jeans and capris though =)
As always great post. =) I still do want to learn how to walk in heels properly but I figure I can work my way up to that hehe.
Nice job on the cute flip-flops
…. Thanks for the compliment and for leaving such a cool comment, let’s celebrate when we both learn to walk in heels 
I’m wearing flip flops right now!
My usual wear is still 4-5inch heals, but they’re boots not shoes, so I gain some stability in that fact as well. Honestly, I’m so terribly used to walking in them that whenever I go outside in flats I feel weird.
It took a while before I even had the nerve to go out in heels, but I don’t even know any better at this point. I don’t think I could go higher than 5″ though. I’m also a short person so I kinda enjoy the added height, lol.
Indoor, beach, warm weather is all flip flops, or barefoot. Besides, you get to show off your painted toenails!
Sweet!
Yes, I’ve found that boots are a bit easier to walk in for some reason. Oh yea, I forgot to mention the exposed painted toenails, thanks for bringing it up
Although heels look great they were hard on my feet, especially if I had to stand for any length of time. Im also around 6′ and heels just made me that much taller than everyone else. I opted for cute flats. There are many styles out there and some are so cute.
I never did get any flip flops yet. My sister,who is over weight ,wore some and tripped over the front of a floor mat at a grocery store. She tore the muscles in her leg and hip and was off work for quite awhile. Flip flops are not overly stable and hard on lower backs. Yes there are better styled ones that have more support and that is what I recommend.
I have only one set of high heels and they are worn little. I have decided that comfortable shoes is my way of dressing. I enjoy going out dressed in skirts but I find flats can be very sexy with almost any outfit. Even at the beach I would wear tennis shoes rather than flip flops.
After saying all this Ill probably get weak and find a cute pair of flip flops I can resist and buy them.
Ouch, sorry to hear about your sister injuring herself. Yea heels look great but there is usually lots of pain to endure to maintain the look. Tennis shoes are the most stable and there are many great styles to choose from
Whili I still love my heels, mostly in the ankle to knee high boot persuasion, I keep them low. I’6’4 as it is, while I’d love to strut around in a nice pair of 5 inch F’ me boots I don’t look at as practical. Besides my girl time as of late is usually spent in denim (colder weather comming just means the capris change to jeans) and my favorite pair of pink nikes my wife gave me. I think I have realized that womens sneakers are acctually ore comfortable then mens.
Yea that’s another drawback of heels, if you’re already tall then they can make you look hulking
… I would love to see a pic of the pink nikes girl 
It has been so long since I last wore heels that I have probably forgotten how to walk in them!
“Keeping this in mind, wear what you want, walk how you want and talk how you want, but don’t do it because you think it’s required, do it because it makes you happy.”
Couldn’t have put it better myself!
Isn’t walking in heels like riding a bike…hehe just kidding, I have no clue
Yeah, when I began my transition, I totally thought I would become a domme femme fatale. Now, I guess I have more of a hippie style, rocking my Birkenstock sandals. But alas, I need to buy some new winter/snow boots soon – it’s about to get really cold here in Colorado.
Cool, I like Birkenstocks
… stay warm out there !
Interesting post, and right on target! So many of our sisters out there dress not as a woman, but their fantasy idea of a woman, teetering around in skyscraper heels for the camera. Fine if that is what floats your boat, but you would be busted in a heartbeat if you went out in public! I like to dress as a real woman around my age would, fairly smart but mostly quite practical too, with low to moderate heels that I can actually get on with the housework in! Actually I take my inspiration for different outfits from women I see in shopping malls and supermarkets. Sometimes I wear flip flops, but almost all of mine have a thick sole and/or wedge heel. Oh yess, and I do have more than enough pairs of 4″ stiletto heels for those special occasions too!
Thanks Sandra
! While I definitely advocate people wearing what they want, there is certain protocol if you want to blend in a little bit more, like observing what other women are rockin’.
I wear them year-round. Yay Florida
Gotta love Florida !
While taking my wife shopping at out local supermarkets in the U.K.
I often look at what the girls are wearing foot wise and dress wise I have found that most are wearing flip flops, sneekers or the new trend are the flat slip on’s. Only about 5 to 10% wearing any heels, seems that the office girls are the ones wearing the heels between 2″- 4″ high.
Not being a girl to go out dressed I like my 4″ or 5″ stiletto heels around the house.
Yea, around the house and out in public are two different things
You know, Martina you reminded of something. When you see so many women out and about in flip flops, sandals and sneakers the women that are in heels seem so much more alluring — maybe that’s just me
Flip-flops are just another part of the slobbing of America. Shorts, T-shirt, flip-flops….you can wear these anywhere whether you are male of female. You won’t get kicked out of any resturants either. “Dress codes” are a thing of the past.
Interesting perspective, thanks for sharing
… When I’m in guy mode I slip on the flip flops to bum around and wear sneakers when I want to look a little nicer 
To me, there is difference between a pair of flip flops, and a pair of thong sandals. Flip flops are cheap rubber shoes, you wear to the beach or pool, while thong sandals are more stylish footwear, made out of leather or some other kind of fabric, and often decorated with some kind of pretty ornamentation or appliqué. Stylish thong sandals, when worn with a fresh pretty pedicure, will look appropriate for almost any occasion. Rubber flip flops on the other hand, are an absolute no-no under graduation gowns, cocktail, or bride’s maid dresses, yet you see ditsy, mostly young women, with no developed fashion sense, wearing them in those circumstances all of the time. Sad! I think it is attributable to our cultures horrible penchant, for uber casualness all of the time.
Melissa
You’re right about that, there are definitely circumstances which call for fancier footwear
Try finding a pair of heels that have a chunkier heel to them so that they’re easier to balance, sort of the way boots help by shifting some of the weight. I have a pair of Mary Janes that I can wear all day without any more suffering than one might get from a pair of men’s dress shoes. I love them. Also don’t go crazy with the height. It’s harder for men to walk in heels sometimes too because our center of balance isn’t in the same place, but a more moderate or even a kitten heel can do wonders.