For an effortlessly classic outfit, dress in an olive bomber jacket and grey gingham wool dress pants — these pieces go really nice together. Feeling experimental? Play down your outfit by rounding off with a pair of athletic shoes. This combination is a smart option when it comes to piecing together a well-coordinated ensemble for transitional weather. You can pay attention to looks like this if you've passed the big 3-0 and you want to take a more mature approach to your personal style.