Tom's Yello Calypso canvas wedge, $69. This is basically a new version of the sneaker pump: Never a good idea! Not to mention the average Toms fan is just not going to be down with this. Comfort is key. And does this mean poor children get a free pair of wedges for every one you buy? I sure hope not.
Even though I only own the silver glitter version, my pick is still the classic, preferably in a dark color.
Tom's Ash Canvas Classic, $44.