Heels. We all love them. From kitten heels to skyscrapers, they’re a great way to complete a look, and can make or break an outfit sometimes. But when you don’t have a pair, or you’ve bought a pair and can’t for the life of you walk in them, you (or at least I) inevitably end up searching online for “Oh hey, how the hell are you supposed to walk in those?!”
As it turns out, it’s reaaaaaaallly not that difficult – read below to learn how to walk in heels with confidence!
A little backstory first, I guess.
Before I’d bought any girl clothes/shoes at all, I tried to simulate what it was like walking in heels. I did this by placing my favourite yo-yo’s flat in the heels of my trainers, and walking around. I say “walking around” as though I was on some kind of charity walk across the country to raise money for children with cancer of the elbow, but in reality it was much more “walk around my tiny bedroom for two minutes and eventually stop from feeling shame and guilt”. Good times. I did eventually walk outside wearing those trainers, and got approximately 100 paces down the road before I became fairly paranoid that someone might question me about my sudden growth spurt of 0.5 inches, upon which I would inevitably collapse into a wailing pile of denim-clad flesh and confess all of my terrible crossdressing misdeeds. So I pretended to have to tie my shoelaces and bent down to slip the yo-yo’s out of my shoes and into my backpack.
I did learn something though, which was this: “Walking in heels – not actually too difficult.”
The common mistake, I think, is that a lot of what people do is try immediately to go from never-having-worn-heels-ever to “YES 6-INCH PLATFORMS FOREVERRR”. While having Shakira as your fashion icon is all fine-and-dandy, jumping in at the deep-end (and in all likelihood, falling over and breaking an ankle in the process) isn’t necessarily well-advised.
Start with low heels
I cannot stress this enough. You’ll be a lot less likely to break your well-cosmeticised face, and it’ll give you the necessary confidence to move higher. The thing is this – if you buy some HIGH heels (and when I say high, even 3 inches can feel very high) and walk around in your house, on your living-room carpet, you can build up a false sense of security. Carpet is disturbingly easy to walk on. Concrete is decidedly not. The transition from carpet to concrete is surprisingly terrifying, and you’d do well to build up confidence with lower heels on concrete first.
Chunky heels are easier to walk in than skinny heels.
Maybe this one is also obvious, but even a few extra millimeters in thickness can make a difference. I’ve got a few pairs of medium-height heels (Ok, I have a LOT, but that’s not really the point). The difference in walkability between the ever-so-slightly-chunkier-heels vs the skinnier-heels is, if you don’t mind a rather obvious pun, staggering. I don’t mean to say that it’s worth going for a shoe where the heel looks like something you might find someone carrying around in a hod, but, again, before you build up some confidence, avoid the stilettos.
Have a good idea of what your shoe size is
If you wander outside, on concrete, in high heels, and even when just sitting on the couch putting them on, you think “Hmm, these are a little bit tight…”, you are going to be in a serious world-of-hurt when you’re five minutes out the door. I kid you not, a SERIOUS WORLD OF HURT. Maybe for us crossdressers, this is a little bit trickier – if you’re like me, and aren’t super great at actually shopping while dressed, buying shoes online can be very hit and miss, especially since shoe-manufacturers don’t seem to know wtf they’re doing RE sizes either. Heels that I’ve bought that have been slightly tight, I’ve stretched out a bit with shoe-stretchers with some moderate success, so that’s helpful at least. But if you’re dead-set on going out into the world and spending some time in heels, PLEASE FOR THE LOVE OF ALL THINGS, MAKE SURE THEY FIT PROPERLY.
Always carry backup flats
I cannot stress this enough.
“You can’t play the flute unless you play the flute” said someone once. Or maybe no one ever – I’m not sure why that quote is stuck in my brain, because a quick google search turns up exactly zero, but the point still stands. You need to practice – whether it’s walking around in your living room for twenty minutes, or being brave and going out into the world (in reasonably-sized, appropriate-height heels), you just kind of have to do it. Technique will come naturally (or at least, it did in my experience – I mean, you already know how to walk, right?)
I’m not sure there’s much else to it! :D