Having a popular brand is often a case of putting lightning in a bottle. Whether you get a high-profile rapper like A$AP Rocky or Kanye West in your gear, or just developed a successful following, if people can't get enough of your stuff, it's a boon for your business. That said—not all popular labels are necessarily good ones. Case in point: Von Dutch. Before Christian Audigier was hawking gawdy Ed Hardy shirts and making a mockery of tattoo culture, he was pushing hundred dollar trucker hats and T-shirts to unsuspecting people who paid the ridiculous asking prices in order to feel cool. Trust us when we say that ten years from now, we'll be looking at some of the "it" brands now and asking ourselves "wait... we really thought that was cool?"