For a casual look, consider pairing a black bomber jacket with chinos — these two pieces work beautifully together. In the shoe department, go for something on the laid-back end of the spectrum and complete this outfit with white leather low top sneakers. This getup is an appealing pick when it comes to a kick-ass getup that will take you from summer to fall. Just because you've passed the big 5-0, doesn't mean you can't dress fashionably, and this ensemble illustrates exactly that.