Cons CTS Low, $60

Luca Says: "The great thing about all the shoes on this list are their simple yet classic shapes. The CTS is essentially a beefed up Chuck Taylor, it holds its shape way better, and in my opinion, looks way cooler than an old-fashion floppy Chuck. The girl that used to give me her leftover chocolate milk at lunch in elementary school always wore Chucks, so Converse shoes hold a special place in my heart, hopefully doing their part in helping to unclog arteries."