The question of what shoes to wear is an important one for baristas. After all, it's a profession that requires many consecutive hours spent standing, usually on less-than-comfortable tile. And so, if you're going to spend 8+ hours on your feet, comfort is an issue, perhaps more so than aesthetics.
Appearances still matter, of course, especially to those who have a certain character to play. You might "need" Toms, or Chuck Taylors, or maybe even cowboy boots, to complete the hipster wardrobe. (Full disclosure: I kinda like all of those options, although I own none of them.)
Old school racing flats, from Puma and Onitsuka (Asics now), seem to be creeping in to the picture as well. I certainly like these options, both for their relative practicality and awesome homage to 1970's pavement pounding (and mustaches).
But speaking of practicality, what does wearing Frank Shorter's old shoes - or any of the other options - do for you? Mostly, they're all relatively level, and feature a featureless rubber sole. Both of these things provide optimal balance and stability. It's not that you really worry about slipping and falling, so much as you'd rather not have to start. And as for the profile, no one wants to spend any length of time standing in even slightly high heels.
Unless you opt for the cowboy boots. Fashion over form, unless there are stirrups at your place of business.
For me, I've yet to find my perfect pair. I've tried on Chuck Taylors, and found them a bit narrow and stiff. As for Toms, I simply can't bring myself to jump on the bandwagon. I'm sure I'd love them, but I just can't. The vintage running shoe look appeals to me, except in that I couldn't stand to get any dirty. I have used my modern Asics Hyperspeed 4's, but the foam compresses over the length of a shift, and the (very minimal) heel raise and arch support become irritating over those same hours.
I've rotated an ancient pair of cheap, Target brand dress-ish shoes with Merrel Trail Gloves recently, with decent results. The former has no traction, and is a bit heavy; the latter is too lug-heavy for tile, and the total lack of cushion wears the legs down a little. Still, both have served well, and will keep doing so, until I'm able to justify buying another pair.
Ideally, I think I want a lighter, more flexible skate shoe. If such a thing exists. They're flat, grippy, and soft - because they're intended purpose requires it. And, not unrelated, they seem to work well for scrawny people in jeans.