Reach for a puffer jacket and a blue denim shirt if you want to look stylish without putting in too much effort. To give your overall look a classier aesthetic, introduce a pair of black leather derby shoes to the equation. This one is a viable option when it comes to figuring out a well-coordinated ensemble for awkward fall weather. So if you need fashion inspo for dressing as you age into your 40s, this combo is a perfect example.