This is solid proof that a black leather biker jacket and navy jeans are awesome when matched together in a relaxed casual outfit. Introduce a pair of black canvas high top sneakers to the equation to effortlessly boost the wow factor of this outfit. So as you can see, it's a seriously stylish, not to mention spring-appropriate, combo to keep in your transitional rotation. Those who wonder how to sport modern casual dressing as you make it through your 20s, this pairing should answer your question.