If you're looking for a casual but also dapper outfit, choose a black leather bomber jacket and black sweatpants. If you want to easily tone down your outfit with a pair of shoes, introduce a pair of red athletic shoes to the equation. On not-so-bone-chilling days, you can wear a variation of this transitional getup and look absolutely amazing. As you see here, after 30 your sartorial options are pretty much limitless.