I have been eying both of those Jeffrey Campbell shoes, especially the Melina's, but worry about comfort. You never know until you try, but in my experience the coolest-looking shoes are often best suited to a low-volume, narrow foot.
Many times I've set my heart on a pair of shoes that look great and would make many outfits pop, only to find the fit is off in some way (usually a combination of tight toebox and loose heels). And unlike clothes, you can't really alter shoes to fit...
And, like Suz, my other big constraint is climate. I have to be strict about not purchasing too many "fair-weather" shoes, because we don't get much fair weather! And the dressy shoes I do buy need to be really versatile, since opportunities to wear them are rare...