This off-duty combination of a bomber jacket and navy jeans is a winning option when you need to look cool and casual in a flash. Want to dial it down in the shoe department? Introduce charcoal work boots to the equation for the day. Keep this combination in your front hall wardrobe come warmer weather, and we guarantee you'll save a lot of time getting ready on more than one occasion. Those wondering how to dress fashionably as you make your way through your 20s, you have your answer.