A brown leather bomber jacket and khaki chinos are the kind of a fail-safe off-duty ensemble that you so desperately need when you have zero time to dress up. Feeling inventive? Tone down your ensemble by sporting white and black athletic shoes. Seeing as temps are dipping, this look appears a savvy choice for the time in between seasons. Just because you're in your 50s, doesn't mean you can't dress fashionably, and this combo proves exactly that.