Hmmm..well, I love heels. I wear them almost every day; they are so much more comfortable than flats and just as easy to walk in. Besides, I have short legs, something I find repulsive, so anything that makes them look longer is a blessing! Flats are actually bad for your arches; a 2" to 2.5" heel is best, whether it's square, wedge, kitten, whatever. That is the best height for supporting the arch without punishing the feet. I only have one pair of shoes with very high heels (I used to have some lovely 6" heels, but wore them out), and they are still easy to walk in. The trick is to put the weight of your foot on your toe, where the shoe is widest (unless you have piano-leg heels on your shoes). When you walk, go ahead and hit the heel first, but get the toe down fast to you have better balance. Walking toe-heel in them is the ideal, and try to walk in a straight line, one foot in front of the other. This also helps keep your balance -- I think many women try to walk in heels the same way they would in sneakers or other flats, and that simply doesn't work! Also, stand up very straight. That will improve your balance (and appearance, too).
Wearing heels for a job where you are on your feet for long periods of time (like my job, teaching) may make your feet ache a bit a first, because you are using different muscles to stand and walk. As an earlier poster said, don't plan on wearing them for hours at first. It's not the shoes, although starting with a lower heel is a good idea! It's like when you being working out -- using those underdeveloped muscles hurts at first, but as you use them more they stop aching.
As for pointy-toe shoes -- if you have to scrunch your toes to fit in them, you're wearing the wrong size. I wear almost exclusively pointy-toed shoes, so I know a little about them. See, your toes are not supposed to go into the point. Look at a pair of pointy-toe shoes. You will see that before the point is the broadest part of the sole. That is where your toes go. The pointy part starts after where the toes are supposed to go -- for heaven's sake, do not stuff your toes into the pointy part! I can only imagine how much that would hurt -- my toes are about the widest part of my feet! (I suppose if your toes shape a point, this would not apply, but I don't know anyone with toes like that.) With a round-toe shoe, this would make your feet look huge, but the point cancels that out. Your feet will look their normal size.
For big feet, try Frederick's of Hollywood for high heels. I had a boss who did drag and that's where he got his heels. He was 6'3" in his flat feet with size 13 feet and he could find well-fitting, classy heels for Madeline at FoH. He also said they were comfortable. One Halloween he came to work as Madeline. We worked retail so we were on our feet, and I asked him how his super-high heels felt after a few hours; that's when he tipped me off about FoH.
Well, this was quite the dissertation on heels! Don't wear them while your feet are still growing; they may cause problems and can deform the foot. If a woman chooses flats, whatever her reason, more power to her. No one should make you wear shoes you don't like -- great shoes are one of the many perks of being a woman! However, if you enjoy heels, they don't have to be torture devices that cause foot, ankle, or knee problems or make you fall over. However, should you ever have to get away from a bad situation, kick off the heels and run barefoot. Some women run just fine in heels, but overall heels are NOT designed for athletic activity.