If I find shoes that fit, they will hurt.
If they don't hurt, they will be ugly.
No shoe without a heel is cute to me, and no heel is walkable. Two inch mary janes send me tottling like a toddler. What is this skill I'm missing? I can do "Tree Pose" in yoga for hours! Why can't I walk in heels?
...and asked for shoe recommendations. My reply was so long, I decided to make it into a post.
High heels are an acquired skill, and not one that many people recommend. High heels are anti-feminist, shorten your achilles tendon, cause bunions, wreck your feet, prevent you from running, skipping, or jumping with ease, and mostly exist to throw out your butt in a sexual way so that sexist men can admire it. They descend in a direct line from Chinese foot-binding, designed to curtail the activities of women. I will not defend my love of high heels as a reclamation of my feminist feminity; they are everything wrong, and more.
They're also beautiful. And they make me feel beautiful. The right pair of heels can take a dress from cute to show-stopping, and I'm short (5'3"), and enjoy being taller, especially when everyone else in the room is inclined to dismiss me as petite and cute*, with nothing substantial to add to the conversation (being able to look someone in the eye is only possible for me in heels).
That being said, the right pair of shoes is very important. Shoes should not hurt you - if they hurt (and not in a "my feet are tired" kind of way, but a "fuck! My toes are trying to secede from my body!" kind of way), they're not good shoes. It is never your fault if the shoes hurt, it is the shoe manufacturer's fault. There are certain brands *cough*Candies*cough* that seem to be made for literal Barbie feet - plastic, permanently formed, nerveless - and should never be worn by actual women.** Good brands will hug your feet and make you glad to own them.
Good brands? Well, everyone's different, but I love Nine West, Steve Madden, and Sofft. Aerosoles makes heeled shoes as well, and I do have a couple of pairs that are okay, but I go strictly on a shoe-by-shoe basis with them, since I've also bought shoes from them that made my instep cramp up after 20 minutes of wear. In fact, all shoe shopping should be done on a shoe-by-shoe basis, I've just had the best luck with the three brands named above. Nine West is far and away my frontrunner in comfortable heeled shoes - I have more pairs of deeply-loved Nine Wests than any other brand.
Now - Nine West is expensive (not the most expensive by a long shot, but regularly more than $100 expensive). I usually balk at paying more than $50 for anything but the most heartbreakingly gorgeous shoes, and I'm happiest when I can get designer shoes at Payless prices.*** Hence, I am a regular at places like DSW and other places that sell designer shoes for cheap. My favourite place is the clearance rack in the back, where everything is even cheaper. I am a cheap, cheap person - I feel really good when I can have a champagne lifestyle, but only if I can get it on a spaghetti budget. You need to visit often, but a good pair of shoes will last you years (I am assuming that I'm not talking to a "must have the latest fashions!"-type audience. It's not possible to be cutting-edge designer fashionable on a budget, at least not any budget I can afford). It's worth paying a little more for a good pair - they'll be worn, instead of languishing in the dark recesses of your closet, and with proper care, will last several years.
Don't be afraid to walk around in the shoes you're planning to buy - take your time, and test to see if there's anything annoying that turns up after a couple minutes of walking. If they pinch now, they'll pinch forever. A good pair of heels does not need to be "broken in" like work boots; they should feel like magic from the first moment you put them on. If they don't, they will never feel good, and you've wasted your precious money. Don't be seduced by pretty bows, or even by a store assistant telling you they're the latest thing and all the cool chicks are wearing them; one guy at a department store looked at me incredulously when I tried on a gorgeous pair of heels and immediately took them off because they felt like concrete. "But they're [Designer brand]!!" he exclaimed. I don't care who made them. If they suck, they suck. And designers aren't all-knowing gods, they're designers. Not all of them understand feet.
Now - how do you wear them? For starters, the stride is different in heels. The step is slightly shorter (at first), and you step with a flatter foot, not heel first. The reason for this is so your heel doesn't hit the floor and skid from under you. As you get used to the feel of your foot hitting the floor (I do suggest trying it out at first at home, in familiar surroundings), your muscles will relax, and it won't feel so stiff and awkward. Also, if heels hurt on you because your toes slide forward, consider platforms - they're often quite gentle in rise from front to back (I have a pair of 5" platform sandals with a mere 1.5" differential from toe to heel).
Now - all that said, heels aren't for everyone. And if you're a flats kind of woman, then I'm behind you all the way. The thing about shoes is choice - all choices are correct (except maybe wearing ratty sneakers to a formal wedding, but I'm not one to judge) (out loud). Comfort is more important than anything. But if you want to learn to walk in high heels, remember that it's like any other kind of physical skill - it takes practice, patience, and a certain amount of protective padding at the start. I have always been in love with heels - I found my first pair in an old bomb site (from WWII - a gap in the houses on a street near my house) at 7, and despite my mother's protests, I kept them, and wore them. I learned to run, jump, and skip in heels - it's possible with practice. I learned also that time in heels must be balanced with time out of heels. Be kind to your feet.
I actually spend most of my time barefoot, and put shoes on only when I have to, or when I'm going out. I have bunions, but they've never hurt - I just have super-bony feet (I have huge pointy ankle bones, too). But my toes are mostly straight, and I refuse to wear heels that shove my feet into tight points - my mother did that for most of her working life, and she had endless problems with ingrown toenails.
Anyway, that's what I know about the Wearing of the Heels.
*Not that I think of myself as either petite or cute. I usually feel like a giant gallumphing thing. Yo, sexism! I got your self-hatred, right here! *gestures rudely*
**Yeah, I own a pair (mules), and I'm fond of them, but they're hell on my feet, and I only wear them places where I'm going to slip them off almost immediately.
***Speaking of which, never buy anything from Payless if you have sensitive feet. They're cheap, they'll last less than a year (I had a pair fall apart the first time it rained), and they have no proper support.