For a look that's street-style-worthy and casually classic, go for a grey blazer and blue jeans. And if you want to immediately step up your look with a pair of shoes, why not add black leather derby shoes to the equation? During the winter months, when warmth is key, it can be easy to settle for a less-than-stylish look. This look, however, is a striking example that you can actually stay cozy and remain stylish in the winter months. So if you're hunting for a modern yet age-appropriate combination for a young gent, this one is great.