This combination of a bomber jacket and skinny jeans is hard proof that a safe casual outfit can still be really stylish. To infuse a dose of stylish casualness into your look, introduce dark brown print leather high top sneakers to this outfit. So if you're on the hunt for a neat winter-to-spring outfit, this just might be it. Wondering how to perfect casual dressing as you pass the big 4-0? This pairing is the perfect answer.