Don't know when to cuff your pants? Well, we're here to show you when and how. The picture on the left, is an example of what to wear when wanting your pants cuffed. This person is casually wearing a plain button down shirt with dark jeans and beige loafers. Remember, you only want to cuff your pants that high when you're wearing shoes that are low-top or ones with no socks. For higher shoes, you should cuff it lower. Watch the video given to see how to cuff your pants.