For an ensemble that's super simple but can be styled in many different ways, rock a brown shearling jacket with black ripped skinny jeans. Inject this getup with a dose of refinement by slipping into black leather casual boots. While dressing for winter can be a bit nerve-racking and time consuming, it's outfits like this that make you feel inspired. This combination shows how to kill in casual dressing as a 20-something guy.