The name says it all: Bootcut jeans were designed to be worn with boots. And if you ask denim nerds, most will prefer a pair of straight-leg to cover their Red Wing or Danner boots. Not only do bootcut jeans flare out and cover sneakers, they often drag on the ground, rip, or fray. This cut of denim should only be reserved for dudes who wear square-toed shoes and tent-shaped “going out” shirts. As someone who takes pride in their appearance, specifically their sneakers, you should never strive to be associated with guys who dress like crap.