To Heel Or Not To Heel? That Is The Question

I have decided that I need a pair of black ankle boots. Nothing unusual about that statement, considering one can never really have enough black boots, but in an attempt to diversify, I have decided that I want an edgier, buckle clad boot. I picture myself wearing this type of boot with feminine dresses and high waited skirts with tops. I can even envision menswear inspired shorts and tights with the boots. Basically balancing the edgier more masculine buckles with softer more feminine pieces. I found two great pairs, both Jeffrey Campbell, and now all that remains is the decision of to heel or not to heel? The advantages to no heel are obvious, my little feet feel no pain, but the advantages of heels can not be ignored either, my little feet look cool and fancy. So, do I choose practicality or a better looking shoe? Let me know what you think. 

Please take note that these heels are wedges that are suppose to be easier to walk in, and they are not outrageously high. Also, please remember that I am trying to wear more heels, but I also don't want to buy shoes that are so high that I'll never wear them. Then, lastly, ponder if you can see me stomping the streets in these puppies. 

Perhaps these are more than practical. Perhaps they are just cool shoes even without the heel. Perhaps you know people at my school don't wear heels, so I would not use heels on campus. Or perhaps you think they are both stupid and terribly ugly. Either way, comment.

General thoughts on this pair? Curtsey of urban outfitters.