Why not consider wearing a black and white houndstooth overcoat and skinny jeans? As well as super comfortable, these two items look great paired together. Add a pair of black dress boots to the equation for an instant style injection. This one is an obvious idea when it comes to a cool summer-to-fall look.
A black leather biker jacket and skinny jeans are the kind of a fail-safe casual getup that you so awfully need when you have no extra time. You could perhaps get a bit experimental in the footwear department and add black dress boots to the mix. On not-so-chilly afternoons, rock this summer-to-fall outfit and look absolutely amazing.