For me, a good bootie is all in the detail. A little buckle here, a knot there, some oxford detailing, a little folding or even just a simple pipe with suede heel. I look at booties as a feature on my foot. Here are the close ups and no, I'm not above buying shoes on the cheap.
For first time bootie buyers, I suggest taking a look at your shoe collection and see what detailing pops out the most. Do you have a lot of shoes with bows? Embellishments? Metallic accents? Use these as your queue when shopping and find a pair with similar features.
Another thing to keep in mind when searching is how the bootie is cut. For people with long legs, disregard because any bootie will look fine on you. I however, happen to have short legs that can very easily look like tree stumps when not featured properly. For those that share the same problem, opt for pairs (examples shown above) that are either cut at an angle, have a slouch factor or are tight at the ankle. If they're neither of those, they're not going to look good no matter what you pair them with.
Once you've got your pair 'o booties, experiment with outfit types to see how they can best flatter your figure. The typical pairings include cropped pants, minis (a-line or straight), skinny jeans/cords, leggings or a-line knee length dresses or skirts. Take note of how your legs look (stumps are never a good thing) and stick with that silhouette whenever wearing.
Here are some examples of good bootie wearing. Happy Friday!