This is what I've learned in my flirtatious dance with my pixie cut. For a longer post with pictures from the different stages of my cut, click here: Evolution of My Pixie Cut
Tips on getting a pixie cut:
Know your cowlicks. It turns out I have at least 5 that I didn't know about...until I cut all of my hair off..They make things problematic. My main one is right in front at my bangs, so I have to fight with it.
You'll learn how to work with them eventually, but don't be dismayed.
Find a model with hair like yours before you get it cut. It helps when you're not expecting something that is impossible for you to get. I kept looking at pictures of women with fine, thin hair and thinking that's what I wanted. I have a large quantity of thick hair and it looked nothing like theirs. Mine is unique and still really cute, but it was still a surprise at first.
Find a really good hairstylist to do your initial cut. We're not talking Supercuts, here.
When growing out your cut, don't go for the "I can't cut it!! I need length NOW" route. This is how you get the mullet stage. The top and sides need to grow out first so keep trimming the back of your neck until the sides and back are similar lengths and you can grow it out as a bob.
You can trim it yourself. If you don't want to look like a homeless man, you need to get your hair trimmed quite often. I usually wanted to every 2-3 weeks...which can get pricey if you go to a hairstylist. Especially if it's really short you can do it yourself with clippers, scissors, youtube, and a lot of patience. It may not be as trendy and cute of a cut as you could get from a salon, but you'll save a ton of money and it will still look cute. I usually do this for trims and every few months I'll go into a salon for a cute style.
Invest in products: There's a huge difference between just letting your hair dry (mine usually gets very poofy and looks like a toupee) and when you put texturizing clay or some kind of product in it.
Take time to style: Depending on what kind of hair you have, (thin, thick, fine, etc) you will still have to take the time to style it, but it will take shorter time than longer hair and will look cuter than a ponytail.
Be bold! If you've decided that a short cut would look good on you, go for it! If it doesn't, you can always invest in cute hats. ;)