This outfit with a black overcoat and grey plaid chinos isn't a hard one to score and leaves room to more experimentation. When it comes to footwear, go for something on the classier end of the spectrum with black leather oxford shoes. This one is a viable option when it comes to putting together a standout look for in-between weather. You can take cues from outfits like this if you've passed the big three-oh and you want to take a more mature approach to your personal style.