From the feet of 1970s punks to the tenth Doctor of Doctor Who, Converse Chuck Taylor All-Stars, often affectionately called "Chucks", have been everywhere. Sure, they don't offer optimal arch support and, since Nike bought the shoe and moved production overseas, the quality is not as fine as it once was, but the look is too classic to pass up. They go well with jeans or casual skirts and even serve as a nice way of toning down dressy pants.

Also, Chucks hold the strange honor of being the only shoe that most people usually like better dirty and worn-in. Pristine new Chucks are actually a bit blinding and scary... But old Chucks with blackened toes, small holes worn in the sides, and fraying laces, instead of looking sad, they look loved, like a loyal pair of shoes that have joined you on every adventure of your life. Have I made it obvious enough that I love my Chucks?

Here's a helpful hint for finding cheap Chucks: While hunting in the clearance sections of shoe stores (or even online, like on eBay), take a look in the men's section as well. Labels on all the boxes are unisex, so no need to convert your shoe size to men's. On more than one occasion I've managed to find a criminally cheap pair of Chucks just because I took the time to peek.