In Her Heels ….Part Un


I know that heels are uncomfortable and some people feel that “women should not wear uncomfortable shoes if they are going to bitch and moan about them. I’m not moaning about them. I don’t wear very high heels all the time, and my daily shoe is a ballet flat.

But occasionally, I like to bust out some cute stiletto heels, and this is for anyone who ever wondered how it’s done, for men and women alike.

I am just the Resident Acting Guinea Pig for learning how to walk in a pair of 4” heels right now, so I thought I’d come up with a primer of what I’ve learned so far.

True story, I once had a newfound tranny ask me to teach him how to walk in stiletto heels.


Before I go ahead, let’s get a couple of basic shoe and foot terms out of the way.

I made a little Anatomy of the foot and Heel for you.

These are just the important parts that I really pay attention to when I buy a pair of shoes.


The yellow spot is where your ball of foot will be. It is the bone just below your big toe that helps you keep your balance.

The higher your heels, the more pressure will be on your ball of foot as your weight will shift forward and put the pressure on that section as you walk.

The lower your heels, the less pressure on the ball of foot.

This is an ESSENTIAL section to pay attention to, if you are learning how to walk in heels.


I just call it the vamp.

The vamp is what covers your toes to hold them in. The higher the vamp, refers to how much material of the top of the shoe, also (called the Shoe Upper or Upper) covers your toes.

Generally, the higher the vamp, the more comfortable the shoe will be.

This is not always the case, because sometimes the material bends or cracks and the vamp of the shoe creates an awful sort of pressure against the top of your foot that leaves a nasty red line or mark, and can cause blisters on the top of your foot.

Any fabric or leather can do that. It just depends on how your foot is shaped and how you walk.

If you buy thin strap sandals, this is especially important because the vamp is what keeps your toes in the shoe itself. If the vamp or the strap of the shoe near the front cuts across your bone and is always rubbing against your foot in an uncomfortable way, or too tight in other areas, then put those beauties back on the shelf.

In sandals, you cannot really fix vamp problems, because the straps expose too much skin to do tricks like wrapping smooth ballet tape around your toes to stop blisters.

Foot Petals came out with these thin straps you put under your shoe straps to keep them on your foot and make them feel comfortable, but… it sounds like a hassle.


The toe box is circled in blue, and the wider the toe box, the more comfortable it will be.

Therefore, square-toed shoes = VERY comfortable, and pointy-toed (but much sexier) = NOT comfortable unless the toe box is big enough.

For very pointy heels, make sure the toe box is wide enough and it’s not just one long skinny point on a shoe. It WILL hurt, and it WILL squish your toes. I guarantee it.

You should almost imagine the pointy-toed shoe to comfortable and be without a point, and your toes should not be squished into unnatural positions into a shape of a point.

This can cause a LOT of orthopedic problems that I get queasy at just Googling images. (I will spare you the pics this time around).

Therefore, make sure the toe box is wide enough as if a point on the shoe never existed.

If you buy open toed sandals or shoes, you are in luck. You will be more comfortable as your toes will have room to breathe and spread out a bit without being confined in a shoe, but be careful of what I call toe overage, where the toes creep over the edge of the heel.

It’s unsightly.

The actual anatomy of a shoe is here if you are interested:


I went over a bit of what to look for in a pair of heels above, but now let’s talk about the height of the heels.

If you buy a pair of cheap 4″ heels, you can be damn sure you are going to regret that decision at 2 a.m. out in the clubs.

Here’s my own personal rule of thumb for shoes at all heights (well, the heights that I’ve worn):

@ 0″ – 1.5″ Heels

A lower quality of shoe is acceptable at this level as your feet won’t be at an angle, and I have some fabric and faux leather heels that are quite comfortable for very cheap.


The pair of faux leather heels featured on the left, were my cheap go-to pair that I bought on sale for $29.99 before tax when I had no money as a college student looking for a job.

I NEEDED heels to wear with my suit (no way could I wear ballet flats), and I couldn’t afford nice shoes at $150+.

The good news is that I wore them so much, my feet literally molded the plastic leather of the shoe, and now they are THE MOST comfortable pair of heels I own, and washed with soap and water (LOL!)

Go figure.

But, it didn’t come without a price.

It took me 3 months of wearing them almost every single afternoon and night to break them in, during interviews and those cocktail meet and greets with companies.

I would come home, take off my heels and whimper at how reddened and painful my toes had become.

If you are willing to tough it out to save $70, my shoes off to you.

So with that being said, I don’t buy cheap shoes any longer.

Sure, if a fabric ballet shoe is cute for $15, I’ll shell out for it, but if it’s a low, faux leather heel, and my feet don’t feel comfortable from within a couple of seconds of wearing them in the store, they go back on the shelf.

I’d rather buy thin, supple leather shoes, but if you can’t afford it the way I couldn’t as a student, stick to a lower heel to save your toes and heel the pain while you are breaking them in.

@ 2″ – 3″ Heels

This is what I normally wear.

You can TRY to get lower quality shoes with 2″, but up to 3″, I’d say you’re asking for trouble.

I am very comfortable in these shoes, and I tend to buy ALL of my work shoes in this size. I know what I can handle comfortably for 8 hours while running around an office, and that’s what I wear.

FB’S SHOES EN POINTE ———————————–>

The shoes featured to the right were around $80 from Aldo Shoes, but the leather was SUPER soft at the toe box, and I knew it could mold nicely to my foot after a couple of wears.

I also put Ball of Foot padding from Foot Petals (sorry for the grossness of the pad, I wear these shoes a lot with black tights).

And the back of the heel, if you look carefully, there’s a grey kind of foam padding at the back made by Dr. Scholl’s and so freaking hard to find (CVS has a nice knockoff copy though).

That keeps my heels in the shoe, and it makes it even more comfortable to reduce the incidence of blisters.

Higher quality is a must at this level if you go higher than 2″.

Nothing special required, just feel the leather to make sure it feels soft and supple so that it doesn’t pinch your toes because it’s too stiff in the toe box, or if the vamp is too high and starts cutting into your foot when you walk.

All that works, is trying on the pair of heels in the store. If they feel tight, pinched, or stiff within the first minute of walking around in them, put them back.

No shoe, no matter what the sale, is worth that kind of headache.

You’re going to spend more time and money in making it feel comfortable than if you had just bought a good pair of heels to begin with.

@ 3.5″ Heels +

This is new territory for me and where I have the least experience. So far, 4″ is my maximum, and I only have one pair of shoes that fit that description.

Where you will have the MOST trouble walking, is not the toes, the ball of the foot or anything. It’s the heel coming down, and the top piece sliding.

If you wear stilettos (thin heels) like myself, you will find yourself a bit teetery when you put your heel down, because if you angle the top piece (the bottom tip of the heel) wrongly as you are putting down your heel, you can end up doing the painful splits without meaning to.

The heel WILL slide, and you just need to rock the confidence to teach yourself how to walk in higher heels by angling the heel correctly as it comes down on the ground so that you don’t slide.

Even top models slide when they walk down the runway. If you pay attention to their stilettos, the heel slides a bit without meaning to.

The 3 most important things to look out for:

  • Vamp/Top line
  • Upper
  • Toe Box and the tip of it

Vamp/Top Line: Make sure it’s of a soft, good quality leather, because this is the only piece that will keep your toes IN your shoe, so your foot will constantly be coming into contact and bending that section.

If it isn’t soft, you will experience pain and possibly blistering from the top line/vamp cutting into your foot as you walk. Remember, these are HIGH HEELED shoes.

Upper: Again, soft, good quality leather is essential at this point. You want to feel your upper foot cushioned without any issues because you will (I imagine) be walking in these shoes some of the night.

Toe Box & Tip of it: This is the most important for me.

Well done shoes, like the ones featured to the left, are actually sloped up a bit at the edge, so that when I walk in these shoes, it helps my toes push off from the ground and lift my heel up to take the next step.

Kind of like a rocking horse motion, see below:


I do pad all of my heels and shoes with some sort of arch, heel and/or ball of foot support because it makes them more comfortable, and it prevents blisters.

I recommend Dr. Scholl’s grey foam padding for the counter of the shoe (the back of your foot’s heel).

They don’t seem to make them any longer (they’re moving to some sort of silicone version I haven’t tried yet because I’m skeptical it works), but I know CVS has a cheap knockoff version of those grey foam heel pads.

DO NOT cheap out on padding.

I repeat.

DO NOT cheap out on padding.

I tried buying a cheap $3 knockoff version of those heel blister foam pads from Aldo, and ended up CAUSING blisters because the pad was made out of some sort of cheap suede leather, and caused more friction than the actual shoe itself.

Awful. I had huge blisters the size of pillows on the back of my foot and I could only wear flip flops in the middle of autumn to let the blisters heal.

My favourite product of Foot Petals is their SOLE STOPPERZ.

These things are brilliant.

I stick them to the bottom of my heels so that that part doesn’t slide, because the textured rubber grips the pavement. Sure, it’s an ugly black spot, but no one sees the bottom of that part, they just see the bottom of the arch of the shoe.

As for ball of foot (the padded, fleshy part just below your toes where if you wear higher heels, your weight comes down on), a pad in the shoe, for that section helps a lot. Foot Petals sells a pair (see above picture)

Other than that, those arch support things don’t really do much unless you are wearing flatter heels or ballet flats.

Head to the Foot Petals website, they sell all kinds of paddings for shoes.


No need to stick to stilettos (I find them to be the most elegant and beautiful of all the shoes), but there are tricks to buying high heeled shoes.

First, don’t buy any with thin stiletto heels. Look for something with a thicker heel, fatter, wider, maybe a wedge instead (but please, let’s avoid the Potted Foot look).

If you are stuck on the look of stilettos, and want a HIGH heel (not something in the 2″ range) look for the platform portion near the toe box that lifts the foot up from the ground so that the vertigo of the foot is not quite as steep, and the angle is more comfortable.

See at the far right of the yellow circle, that 0.5″ of platform? That helps me walk in these heels which are 4″ high, but are now 3.5″ instead.


Wearing high heeled boots is a lot easier. There is more fabric wrapped around your leg and foot to keep the boots on your feet, and .. I just find them sturdier and easier to wear.

You could train on these, and then graduate up to a thinner heel in a boot, then try heels after that.


Like I said. DO NOT wear 4″ heels every day, or you will be going in for some expensive foot surgery to correct the problems.

I wear 4″ heels only once, maybe twice a year for 5 hours each time.

The rest of the time, I am in comfortable, structured ballet flats that give good foot support, or in lower heels.

I try not to wear heels often. I don’t want to hurt my feet and do all sorts of nasty things to my joints just for beauty. But once in a while, the high stilettos come out.

About the Author

Just a girl trying to find a balance between being a Shopaholic and a Saver. I cleared $60,000 in 18 months earning $65,000 gross/year. Now I am self-employed, and you can read more about my story here, or visit my other blog: The Everyday Minimalist.