The Art of Wearing Heels

I started wearing heels when I was 14. I had no clue how to balance correctly in them, no clue how to walk at all, and probably looked like a complete and utter moron. 8 years and at least one major injury since then, I wear almost nothing else. Not always by choice... primarily because my major knee problems are exacerbated by wearing flat shoes for extended periods of time.

So, some thoughts on wearing heels, and doing it right:

1. BALLET FLATS ARE BAD FOR YOUR FEET
This is not to say all flat shoes are bad for your feet. But those trendy shoes with zero arch support? Yeah, you're actually BETTER OFF in heels. Two years of working at Famous Footwear taught me all of us who suffered from plantar fasciitis couldn't deal with wearing the "ballet flat" look.
Here's the deal: plantar fasciitis is becoming more and more common (or I'm just meeting more and more people who suffer from it)... and though the most commonly known symptom is heel pounding and subsequent heel pain, the true cause is fallen arches. Wearing ballet flats is NOT like walking on bare feet... when you're walking barefoot, you're using all your muscles correctly (most of the time. Some of us are unfortunately screwed up)... when you're wearing shoes with no arches, your feet are being stretched out, and if you're prone to fallen arches, you're actually hurting your feet.
On an average shopping trip, I find way more heeled shoes with arch support than flat shoes. Plus, simply by raising the heel higher than the toes, the shoe is forcing your foot to curve. I may stick by Converse when I need sneakers, but when I need to dress up, I will choose heels over flats ever time.

2. KNEE PROBLEMS? HEELS MAY BE MORE COMFORTABLE
The key here is testing every pair for comfort and correct height. I personally am missing a substantial amount of cartilage in one knee... though I can wear converse or really supportive flat boots in small doses, I can't wear anything flat for extended periods of time or for heavy duty use of my feet(this includes work.) Hell, even hiking and running shoes have a raised heel on them. For starters, pushing your knee forward can help prevent hyperextension, or if you're lacking as much cartilage as I am, the daily worry of having your kneecap sink back in on itself (which, while not as painful as hyperextension, can cause some really uncomfortable cramping and make walking quite difficult.)
In the case of sports shoes with a raised heel, this is actually to help absorb shock. Your heels do get a lot of impact from activity, and not only does it wear at your heels, it can also shoot up your legs to your knee. Ouch. I choose heels.

3. PICK THE RIGHT HEEL HEIGHT
A huge part of wearing heels effectively is knowing your height range. I personally won't go any higher than 3.5", and even that is pushing it (just one pair of shoes, and I don't wear them if I need to be walking a lot.)
Go any higher than your maximum heel height, and not only do you risk back problems, you look like an idiot.
No joke, I make fun of girls I see in bars teetering on way too high heels. If you can't walk without looking like a complete and utter moron, pick a lower pair. The end. If you don't? Well, you were warned. I am mocking you.

4. TEST FOR GIVE IN HEEL
Remember that bit about how much shock is absorbed by your heels? Lifting your heel off the ground won't help with that if the heel is hard as a rock. Avoid spiky stilettos (you're standing on a thin thing that's digging directly into your heel), and make sure the heel itself has give.
When trying on a pair in the store, rock back onto one heel and push your weight down (make sure your other foot is flat on the ground or you may fall over)... if there's give, you're ok. If there's not, try again.

5. START THICK, GO SMALLER GRADUALLY
I first started with thick, chunky, square shaped heels. I eventually gave up on these, largely because they make the shoe heavier and therefore more effort to walk in. Still, having a stable balance makes it way easier to learn to walk in heels. And never, ever go all the way to stilettos. I now do slightly thicker heels, kitten heels, anything I can balance in. But your balance will be so much better if you start by wearing heels where the heel itself spans the whole width of the heel of the shoe.

6. FIT IS EVERYTHING
I've fooled myself into buying horrid fitting heels before. And I have ALWAYS come to regret it.
Let's examine how terribly screwed up my feet are:
My left foot fits best into a 6.5 regular. My right foot fits best into a 6 wide. Most shoe stores will NOT mix sizes. I'm generally ok if I stick with 6.5s that run wide through the toes and narrow through the heels. Both my feet usually end up happy. It's when I've gone for 6.5s that are really wide through the heels, or unfortunately narrow through the toes, or even tried going up to 7s because it was the last pair, or it was wide enough, or whatever dumb reason I had.
Think about how much weight you're resting on your toes... then think about how important it is to avoid pressure points, having to grip extra hard to keep your shoes from falling off, etc. If it doesn't fit, it doesn't matter how cute it is... I'm never going to wear it again.

7. PRACTICE, PRACTICE, PRACTICE
When I was 14, I was stumbling around like a moron in 1.5" chunky heels. At 22, I rock 3.5" heels like a pro. I get compliments on my shoes, people express surprise at my ease and comfort walking in heels, and I get to make up for my negative feelings about my short legs on a daily basis. No one knows how to walk in heels the first time they try. Or the first year after that. Just make sure you look balanced and poised while doing it, or you're better off staying low to the ground (but, you know, avoiding ballet flats at all costs)