I can't remember the last time I went on a trip—be it a weekend getaway to the weirdest spots in the U.S. or a two-week long vacation to Shanghai—without at least two pairs of boots. Some say I might have a problem, which I admit, but I have never regretted the extra bulky carry-on (bursting at the zipper) transporting my beloved Chelsea boots or Dr. Martens. And since I wear boots on a daily basis, they get worn and damaged pretty quickly. That's why I am such a fan of super cheap boots that look expensive (and I'm pretty sure the rest of the world is as well). To help everyone get the boots of their dreams without breaking the bank, I rounded up 50 super rad boots under $100. Peep through the gallery and get shopping.