This article was written for us by one of our clients, Davina. Thank you Davina for sharing your advice and experience!
High Heels 101
So you’re thinking of dumping those boring flats for some sexy stilettos? Don’t be afraid! Here’s everything you need to know about wearing high heels (and you can skip to the bottom of the article if you only have time for the short version)…
Get to know Davina
First, a little bit about myself, for perspective: I’m a middle-aged guy who only recently got into cross-dressing. For many years, I had a bit of interest in cross-dressing, but I never did anything to satisfy or explore my curiosity. Then one fateful day, 6 months ago, I discovered The Breast Form Store’s website. OMG has that ever changed my life! Sure, I’m still just the same old regular dude 99% of the time, but TBFS has done an incredible job helping me discover (and bring out) the woman in me, and it’s been an incredible amount of fun. TBFS has a seemingly endless selection of quality products (at great prices) for every TG/CD girl, but even more than that, the wonderful service that I’ve got from the people at TBFS has enabled me to get in touch with a feminine side that I didn’t even know I had. Besides shamelessly plugging my favourite store, why does any of that matter? With regard to high heels it’s important to note all that for two reasons:
- Since I’m a new and only occasional CD I cannot offer advice on how to wear high heels for 8 hours a day at work, every day, because I’ve never done anything close to that.
- Readers should take encouragement and inspiration from the fact that though I’m very much new to high heels (and late to the party), I can easily prance around in 5” stilettos with confidence as though I’ve been doing it for years.
I doubt that many trans women or long-time cross-dressers will learn anything new in this article – you girls have already got heels figured out on your own, so you don’t need advice from a noob like me. If you’re brand new to dressing and don’t know how to pick out heels (or walk in them), if you’ve never worn heels and want encouragement, if you’ve dressed for years but you’re just starting out in heels and want some tips, or if you want to push your limits with some sky-high stilettos to look and feel sexy for a special night out (or in), read on!
Physically speaking, at 5’-11” (180cm) and 175 lbs (80kg), I’m about as average as it gets for a guy (but I DO have great legs that look fantastic in stockings and heels!!!) I consider myself to be reasonably fit, and have decent balance, however I certainly wouldn’t call myself an athlete. I’m no spring chicken, either, and I’m not as limber as I used to be.
I typically wear a size 11-11.5 in men’s shoes. My feet are a bit on the narrow side, which means I sometimes have trouble getting a good fit with men’s shoes, but the upside to that is that it sure helps me fit into women’s shoes with ease! Finally, it’s worth mentioning that my lower legs and ankles are a bit slimmer than average. Much of the advice here applies to girls of all shapes and sizes, but it is important to know where it’s coming from.
The math says you can do it!
It would make sense to presume that men would have a more difficult time walking around in high heels compared to women. After all, women have wider hips and a lower centre of gravity than men, making them more stable and better suited for heels. Add that most women have been wearing heels (at least occasionally) for years, while most men have not, and heels can be intimidating to the first-timer. In reality, men (or anyone with longer feet) actually have a big advantage over women (or anyone with shorter feet). We can call it our little secret, but high-school trigonometry reveals it, and it’s obvious once you think about it. Simply put, given a particular heel height, as a foot/shoe gets longer, the angle (slope) of the shoe gets lower (and therefore easier to walk in).
Crunching the numbers reveals that a shoe with a 5” heel in a size 13 is no steeper than one with only a 4” heel in a size 7! A size 13 with a 4” heel is barely any steeper than a size 7 with a 3” heel. And a size 13 with a 3” heel puts the foot on the same angle as a size 7 with a 2½” heel. So right off the bat, if your size runs into the teens you’ve got an advantage over girls with single-digit-sized feet!
How to walk in heels
Before getting into how to walk in heels, I should mention at this point that when you start wearing high heels it is important that they fit well. You may need to experiment a bit to find your perfect size and like any kind of footwear, a size that is perfect in one brand / model / style may not work in another. This depends somewhat on your intended purpose for the shoes: If you plan on wearing them all day, then they better fit well and be comfortable (maybe you should buy them a little larger so that you can use insoles and other padding inside the shoes). If you’re only going to wear them for a couple of hours (and you’re not going to be doing too much walking), you don’t really care as much how comfortable they are, just as long as they look fabulous! And let’s face it: if they match your outfit perfectly, you’re probably willing to put up with a bit of discomfort knowing that you look great. More on this later.
Prior to 6 months ago, I hadn’t taken a single step in high heels in my entire life. When I got my first pairs of heels from TBFS (two pairs of 3” sandals and one pair of 4” pumps), I was nervous about whether or not I’d be able to walk or even stand in them. I absolutely LOVED the look, but would I be able to take more than a few steps without twisting an ankle or falling???
I started off with my cute silver Pleaser Kimberley-04’s. They were a perfect choice, a 3” wedge heel sandal, and I took my first few tentative steps. I knew enough to focus more on standing tall and keeping my balance rather than walking at first, but soon started gingerly walking around and getting comfortable. It didn’t take me long to realize that heels weren’t anything to be afraid of!
Be confident, stand tall, keep your head up and look forward. Take smaller steps than you would in men’s shoes, and let your arms and hips flow and sway a bit. Put one foot in front of the other, almost so that the path of your feet make one straight line (rather than your left and right footpaths making 2 parallel lines). Another way to think of it is imagine you are walking on a balance beam (or walking a line for a sobriety test) – just look at how supermodels walk in heels.
Always remember, on hard flat surfaces, it’s heel-toe, heel-toe, heel-toe. As you step down with each foot, make sure that the heel comes down slightly before the toe does, then transfer your weight to the ball of that foot to push off for the next step. You’ll know you’re starting to do it right when your walk makes that sexy rhythmic high-heeled clack, clack, clack sound.
If you’re struggling at first, put your regular shoes back on, and practice by standing and walking around on your toes. Do some calf muscle exercises while you’re sitting or lying down by pointing and relaxing your feet and toes as much as you can to get those calves stretched. Then put the heels back on when you’re a bit more loosened up. If you’re having trouble and starting to get discouraged, take a break! Come back to it in an hour (or a day) – there’s no rush.
Before you know it, you’ll be confidently strutting around in your heels. Don’t get too confident, though! Now that you’re comfortable walking around on flat surfaces, it’s time to point out that you’re only halfway there! You’ve also got to learn how to deal with stairs and soft or unpredictable surfaces when you’re wearing heels. Unfortunately, much of what you’ve learned and perfected for walking around on a hard flat surface goes out the window when you get to stairs and uneven or soft surfaces, so just when you think you’re getting the hang of it, you’ll need to learn how to walk in heels for a second time!
Make no mistake, going DOWN a flight of stairs is probably the most difficult (and dangerous) thing you’ll do in heels. In heels, you will NEVER hurry down stairs like you can with flats, no matter how comfortable you get. Once you get to a set of stairs, you need to completely rethink your approach and throw out the heel-toe mantra that you’ve perfected for walking on a flat surface. You can either walk down stairs by putting your weight on the balls of your feet (as though you were standing on your toes), or you may prefer to put both your heel and toe down at the same time. Experiment – CAREFULLY – and ALWAYS hold onto the handrail. GO SLOW! You are not going to be quick (or graceful) the first few times you do this! Importantly, make sure to put your heel down close to the riser (the vertical part of the step), to ensure that the ball of your foot (which carries all your weight) is safely on the tread (the horizontal part of the step).
Depending on the size of your feet, you might even prefer to walk down stairs with your body (and therefore your feet) turned at a slight angle to be sure that the ball of your foot is safely on the step. Walk down the stairs slowly, and use the handrail as you do it. With a bit of practice, you’ll be able to gracefully walk down stairs in high heels, but you’ll never do it as quickly as you would with flats, so don’t even try. When you walk down a flight of stairs, think of yourself as “making a grand entrance”. Would you rather go slow and be stylish and graceful, or go fast and fall on your face? Normally while walking in heels you want to hold your head up high and look forward, but when you get to a set of stairs you’ll want to have a quick look down at your feet to see how/where they fit on the first step or two. Just be careful, as this is the hardest thing to master in heels! In fact you may not ever master it – you might have to be satisfied with just doing it safely and hopefully with a bit of grace. And I’ll say it one more time: USE THE HANDRAIL!!! The handrail will help steady you, and could save you from a fall if you miss-step. It’s not there just for decoration!
Going UP stairs fortunately isn’t nearly as hard as going down, you just need to remember one thing: walk up stairs as though the heels fell off your shoes! Put all your weight on the balls of your feet (as though you were standing on your toes), and walk up the stairs like that. Keep your head high and look forward (not down), though it’s perfectly OK to glance at your feet occasionally while you’re learning. Your heels might not touch the steps at all, and they may even be hanging over the front edge of the steps… it doesn’t matter, because you’ve got all of your weight on your toes / balls of your feet. Going up is a lot easier than going down. One more thing: just like with going down stairs, USE THE HANDRAIL!!!
When you get to uneven surfaces, soft surfaces (like lawn), and surfaces with openings (like grates), use the same technique as you would for going UP stairs. Put all your weight on the balls of your feet, as if you were standing on your toes, and walk. That will keep your heels from sinking into the ground, or pushing through a grate, and tripping yourself.
If you live in a colder climate, you might be wondering how to walk in heels when you’re faced with snow and ice. The answer is simple: DON’T. High heels are simply not appropriate for those conditions, end of story. Wear some sensible winter boots, bring your heels along, and change into those stilettos once you’re safely inside.
If all this comes off as discouraging, it isn’t meant to. Walking in heels takes a bit of practice, but once you get the hang of it you’ll love it! Just don’t forget that there’s one technique that you’ll learn for walking on firm flat surfaces, and there’s a whole other technique you need to use for stairs and uneven/soft surfaces. On firm flat surfaces you will likely quickly gain confidence and feel as though you could jog and sleepwalk in your stilettos. For everything else, though, you’ll learn to take it slow and be careful. Always be aware of your situation, and the ground under your feet, so you know which technique you need to use.
One last thing to keep in mind with heels: walking in stilettos is a bit like riding a bicycle – once you get the hang of it, it’s not hard to get back into it even if you haven’t done it in a while. Part-timers need to remember, though, that if you’re only occasionally wearing heels, give yourself a few minutes to get comfortable in them before rushing out the door.
After practising all the above techniques, I was having a lot of fun prancing around in heels, but I did run into one problem: I kept looking down at my feet, to try to see how they looked walking in heels. This was trouble, as there’s no way you can walk properly while staring at your feet. I learned to keep my head up and look forward. A full length mirror at the end of a hallway is perfect if you want to see how you look walking in heels and still be able to properly keep your head up.
Going with higher and higher heels
In no time, I was walking around in 3” and 4” heels like there was nothing to it. Back to TBFS I went to put in another order and I got myself more shoes, some with 5” heels!!! When those beauties arrived, I very quickly got comfortable walking around in them, too. By this point, I realized that I really had a thing for shoes! I wanted to challenge myself with even higher heels. Another order with TBFS, and another discreet plain brown box arrived filled with more beautiful shoes – the ultimate being a crazy sexy pair of ankle strap sandals with 2¾” platforms and 7” stiletto heels!!! I tore open the box, strapped those beauties on, and immediately started strutting around with ease! And to think, only 6 months ago I had never even worn a high heel, let alone walked in one.
Everyone has their limit as to how high they can safely and graciously go, and (for now) I have met my match with a pair of red Devious Domina-420 6” pumps (all heel, no platform). They fit great, look absolutely stunning, and I could stand around in them for hours. But walking in them? Well, let’s just say that I can carefully make my way around wearing these beauties, but I don’t look very graceful doing it! That doesn’t mean that I’m going to get rid of them – oh, no, these gorgeous shoes aren’t going anywhere! They look sexy (even if I can’t walk very well), and if nothing more they will always be something for me to aspire to. Besides, with a bit more practice I should be able to work up to them, and I view them as a challenge that I will overcome.
Fit & different styles of high heels
A very important aspect of high heeled shoes is fitment. In fact, that’s the most important thing. Running shoes aren’t much good if they don’t fit, so imagine how important it is for shoes to fit when they’re stilettos! You might have to experiment a bit to get heels that fit you perfectly. I haven’t needed to use it, but it’s worth noting that TBFS has a good return policy for shoes. Plus, TBFS staff would be happy to help you get into the right size. Regardless, when you start having fun building a collection of heels, sometimes how comfortable they are is less important than how good they look!!! You can always go back to those boring flats if you need comfort. High heels are all about style and looking sexy!
Often when you get a brand new pair of heels, you will notice that the bottoms of the shoes are shiny and slippery, so keep that in mind when you’re wearing a pair for the first few times. As you wear them, the bottoms will get scuffed and will grip better. If you want to speed up the process, you can scuff the bottoms with a bit of sandpaper. Just be careful not to damage any visible part of the shoe.
You have some flexibility with high-heeled pumps. It’s very important that pumps fit well – a bit too tight and they won’t be comfortable enough to wear for very long, a bit too loose and you’ll walk right out of them! At least with pumps, though, if they’re a bit too small you can usually stretch them a bit (search the internet), and if they’re a bit too large you could wear an insole, or maybe cut the toe ends out of a pair of socks and put them over your toes inside the shoes. It goes without saying that if your pumps are way too loose, putting on a pair of heavy wool socks is not the answer – that just doesn’t look sexy at all! No girl’s wardrobe is complete without at least one pair of classic pumps, and they’re available in every colour of the rainbow. Heck, they’re even available IN rainbow colour! Classic pumps come with everything from kitten heels to 6” stilettos, and some have platforms to get you even higher – go as high as you dare! In addition to classic pumps, you can get pumps with ankle straps, and of course there are plenty of cute Mary Jane styles with straps. The bonus with Mary Janes is (besides looking adorable) the strap helps hold your foot in the shoe securely.
When it comes to sandals, the slide on ones look great, and are easy on/off, but I don’t have any (for now, anyway) so I can’t offer any insight. I do have several pairs of strappy sandals, though. For your first pair of sandals you might want to stick to ones with ankle straps if you’re planning on doing a lot of walking. The straps are adjustable, and help hold the shoe securely to your foot. It’s also worth noting that with my narrow feet I find that going down a half or even a full size from what I wear in pumps yields a good snug and secure fit for open-toe sandals. Nothing shows off a nice pedicure and cute toenail polish like a pair of open-toe sandals. Every girl needs at least one pair, and when you see all the different styles and colours, there’s no way you could (or should) stop at only one pair!
High-heeled boots and booties are a really good option to consider that look great, go with a variety of outfits, and offer way more ankle support than pumps and sandals. For this reason, every girl should try at least 1 pair of high-heeled boots. These are the closest you’re going to get to a shoe that fits and feels like a man’s shoe (except for the high heel, of course).
Then there are styles of shoes that are hard to categorize, like the gorgeous pair of Pleaser Delight 600-14s that came in my most recent TBFS order. You can call them an open-toe sandal, but they have an open heel / open front upper at the back of the shoe with wide laces on the front. Pleaser also calls them a bootie. I call them sexy, and the high front lace-up means they’re really secure. These might be my favourite pair of heels at this moment, but with a 6” heel and 1¾” platform they’re not for every girl!
In my case, I have a relatively narrow foot and usually wear a size 11-11.5 in men’s. Depending on the website you’re looking at, you may see the general advice to add 2 sizes to convert from men’s to women’s or you might see 1.5 as the number to add. Women’s shoes are often a bit narrower than men’s, which is not a problem for me but might be for many others. Wide widths are available in many stylish high heels. I have found that size 13 fits me great in a variety of pumps, and I prefer to go down to a size 12 for open toe/heel sandals so that they fit me securely (though 12.5 might be the perfect fit, heels are often not available in half sizes). On account of my skinny ankles, with pretty much all of my heels with straps I have found that the straps were not tight enough to serve any purpose (other than look good). The easy solution is to poke a few extra holes in the straps or, as I did, carefully use a power drill with a small drill bit. Some extra holes in the straps made the difference, and now all my heels fit perfectly and securely.
The key is accepting that you may need to experiment a bit with sizing to get shoes that fit you well. I’m sure the fact that I have narrow feet influences my experience with high-heeled shoes. Girls with wider feet may have to go up an extra size (or stick to wide-width heels). You may also need to “tweak” the shoes a bit (add padding, etc.) to make them work for you. You may need to put some padding in the toes (because that’s where all your weight will be concentrated). It all depends on your intended use of the shoes. Planning to wear them all day long? They need to be comfortable and probably a more moderate heel height. Just looking for something to go with a particular outfit and you won’t be wearing them for more than a couple of hours? Go as high as you dare and be willing to sacrifice a little bit of comfort if they look great. It goes without saying that just like any type of shoe, high-heels will get more comfortable as they get broken in – just don’t expect them to feel as good as your favourite slippers. You rarely get something for nothing in this world, and with high heels you are willing to give up a little comfort to gain sexy style.
Heel & platform heights
As far as heel height goes – don’t be afraid to try to go a little higher, but be careful and give yourself time to adjust. While I firmly believe that anyone can easily prance around in 3” heels (with a bit of practice), going up to a 4” or 5”+ you’ll eventually reach your limit. You may reach that limit rather abruptly, too: A 3” heel feels like flats to me, and I could literally go jogging in my 4” pumps and enter a walkathon in my 5” pumps. In my all-heel 6” pumps, though, I suddenly look like Bambi taking his first steps. I’m sure with practice I’ll get better with them. In the meantime, my 6” stiletto pumps look gorgeous, but don’t ask me to walk too far in them!
Also worth talking about are platforms. Platforms add height to the entire shoe with a wedge of sole under the ball of the foot and toe area. This increases the heel height for a given angle of shoe (reaching dramatic stiletto heights) yet does it in a shoe you can actually walk in. A good example is the pair of Pleaser Adore-709s that I just got. They have a 7” heel, which would be impossible to walk in without a platform. Since they have a 2¾” platform, though, the slope of the shoe is really only as if it had a 4¼” heel. So despite having a ridiculously sexy 7” heel they actually have the walkability of a 4” heel. They’re easy to walk in and certainly attract attention, but are obviously not for the faint-hearted, nor are they an appropriate choice for your first pair of heels!
Speaking of those Adore-709s, you might be worried that you’d be too tall wearing heels. I say WHO CARES??? GO FOR IT!!! At 5’11” in my bare feet, I’m the tallest girl in the room by a long shot when I’m wearing my 7” platform stilettos. I tower over most WNBA players! But I look fantastic and feel great, and that’s what matters!
Sky-high stilettos will make you taller, maybe too tall for your liking. There’s no denying that, and you may be worried that you don’t look as feminine as you get taller. What may not be obvious, though, is that as you move up to a higher heel, your feet actually look smaller. If you want to picture it, stand sideways in front of a full-length mirror and look at your legs and feet. Look away, stand on your toes and look back. Your feet look a lot smaller when they’re on a steep angle while you’re standing on your toes, and that’s how it works when you’re wearing heels! A perfect example is my Pleaser Seduce-1020 lace-up ankle boots. With a cute little pointy toe, and a 5” heel (no platform), these adorable boots make my size 13 feet look positively dainty (and feminine)!
Recap
Here’s a recap of the most important points about heels:
- Get shoes that fit, both comfortably and securely. Scuff the bottoms of new shoes for better grip if you need to.
- Start small and work up, don’t go for the 5” stilettos right away (they’ll only look good until you twist an ankle or fall).
- Given the same heel height, wedge heels are easier and more stable than block heels, which in turn are easier than stilettos.
- Be confident, stand up straight and tall, keep your head up, and look forward.
- Take smaller steps and let your arms and hips sway a bit.
- When you walk, put one foot in front of the other, so that the path of your feet make one straight line up the middle (rather than your left and right footpaths making 2 parallel lines). Walk as if you were on a balance beam.
- When you’re learning to walk in heels, take a break if you’re struggling. This is supposed to be fun, not frustrating, and you’ll get it (eventually).
- Always be aware of what type of surface you are walking on, and adjust your walking style to suit.
- For hard flat surfaces remember: heel-toe, heel-toe, heel-toe. As you step down with your foot, make sure the heel comes down slightly before the toe, then transfer your weight to the ball of your foot to push off for the next step.
- For everything else, slow down, put your weight on the balls of your feet, and be careful.
- Be extra cautious with stairs, especially going down. Keep your weight on the balls of your feet and make sure the main part of your shoe lands on the step. Take it slow, and use the handrail.
- You’ll be strutting around in heels in no time, and you’ll be rewarded for doing it right when your walk makes that rhythmic sexy high-heeled clack, clack, clack sound.
There’s one last thing I should mention: The Breast Form Store has a great selection of shoes, at great prices. But did you know that TBFS can order anything from the entire catalogue of Pleaser shoes??? I asked TBFS and found that out – I was thrilled, but my credit card took a beating! So if there’s a particular style of Pleaser shoes that you don’t see on TBFS’s site, send TBFS a message or email and they can probably get them for you.
So what are you waiting for? Give those boring flats a rest and try out some heels! Maybe you’ll only end up with a couple pairs of kitten heels that you wear with certain outfits or for special occasions. Or maybe you’ll end up with a whole collection of heels for every mood, situation, occasion, and outfit. Heels make a plain outfit sexy, and put a sexy outfit over the top. Wearing high heels changes your entire posture and how you stand, walk, and move about – in a good way. You simply can’t fall back on your instinct to walk “like a man” when you’re wearing a pair of stilettos, and besides changing your appearance, wearing high heels changes your whole attitude. You may have your hair and makeup done to perfection, and be wearing the cutest dress in the world, but nothing SELLS IT like a stylish pair of heels. The look and the way you move… There’s nothing more feminine than a killer set of heels. If the shoe fits, wear it! Just make sure there’s room in your closet for more!
This article is extremely helpful and although I have been wearing and practicing everything this article mentions, for quite a while, (through trial and error), I still find the tips very useful. I also found it fascinating and true, about the (ratio) of heel height and length. I never thought of it in that way, but now realize why my 14 women’s size doesn’t look as large as one would think on my foot. In addition, I tried that little experiment of standing sideways in front of the mirror to be right on the mark.
Over the past years, my shoe collection has grown in a way that I would never have expected. From flat sandals, to 5″ (being the tallest I feel comfortable in) Pleaser heels, and almost everything in between. My feet are on the wide side, and over the years, I have discovered that shoes sold by Torrid tend to work a little better for everyday wear. They offer wide selection of wedge, block, boots and booties, in addition to stiletto heels that I feel are very feminine and flattering. Some of their heels have a wider less pointed stem, and as pointed out in the article, have a wider toe box which makes balancing on the balls of the feet and little easier. Which in turn inspires confidence when going to a higher (and sexier) heel or platform.
Thank you for the wonderful article and suggestions.
A Good Way To Start Is With A 2″-3″ Block High Heel… That’s What I Did, Now I Wear Many Heels Pumps,Various Boots & Booties,Heeled Sandals..
Great article. The one part that stands out to me is to practice walking on your toes is a straight line. That technique made me feel comfortable in high heels. Small slower steps as well.
yes the higher the heel the better we look, I wish that My collection would grow I only have 3 pair and one is a over the thigh 4 inch boot-0 awesome look and so comfortable= Val Q