“She told me to walk this wayyyyy…”

One thing I wondered about when I started cross-dressing was what the hell I was going to put on my feet. It wasn’t long before I realised why certain women go nuts when it comes to footwear.

Shoo away
The first thing a cross-dresser should know is that you don’t have to wear heels. Really; you don’t. Take a look at a busy street in the middle of the day and see if you can figure out the proportion of women wearing heels. It’s pretty damn low. Heels are uncomfortable, impractical, and unsuitable for a variety of surfaces and gradients.

If you’re starting out, it’s a better idea to figure out what style of footwear goes with the rest of the clothes you’re acquiring (a quick, handy guide can be found here). Does the colour match your outfit? Or will you take the easy option and just go with all-black footwear?

How much into crossdressing do you want to go? Do you want to have a different pair of shoes for every outfit, or do you just want a few different styles that will cover all possibilities? (I ended up with just three pairs of boots -one flat, one with stiletto heels and one with insane four-inch heels- and two pairs of heeled shoes.)

It’s also worth considering where you’re going and how much walking or standing about you’re going to do. I can attest that walking on cobbles in heels is a bit of a sod, and that if you’re going to climb eight storeys of stairs in stilletto heels, you’re going to have a bad time. The longest I spent in heels was 14 hours, and I regretted it for days afterwards. So, if you want to try to look glamorous, go ahead; just be aware that you’ll pay for it…

These boots were made for walkin’
Even with only fifteen dots on a black background as a guide, it’s possible for us to identify the differences between a ‘male’ and ‘female’ gait. So, if you really wanted to present yourself as ‘feminine’ as possible, you’d have to learn how to alter the way you walk. This doesn’t mean walking like a runway model, but it could mean making some subtle adjustments to your, pace, stride and posture. (If you want to play about with different walk styles from the comfort of your chair, I strongly recommend giving the BioMotionLab walk simulator a go.)

Brought to heel
Personally, I think there’s something oddly empowering about walking around in heels. There’s the gain in height, the loud clack (or scrape) as they hit the ground, and the shift in posture they bring. And if you can walk in heels confidently, you’ll earn minor kudos. Bear in mind that men are heavier than women, so heels may not support your weight. And, like most things in life, don’t overdo it.

One tip I was given for learning to walk in heels was to do vacuuming around the house in them; in the process, your feet and ankle joints will go through a full range of motion in them, helping you to acclimatise. And you’ll have clean floors, too, so hey – that’s a bonus. My girlfriend once returned to find me doing this, and you can imagine her surprise. Not that I was wearing heels; that I was doing the vacuuming.

If you’re at all unsure, film yourself and see how you look. Try to find something that feels comfortable; if your gait is natural and easy, you won’t draw attention to yourself in a bad way.

Sometimes, though, you just need to make a complete tit of yourself in public in order to learn to do better the next time. This is me walking in smooth-soled heels on the polished, curving deck of a boat:

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