Nail the laid-back and cool getup in a red and black check flannel long sleeve shirt and black jeans. Hesitant about how to round off your outfit? Round off with dark brown leather casual boots to polish it up. When it comes to dressing for weird fall weather, nothing beats a neat combination that will keep you toasty and looking your best. This pairing proves that well into your 40s you still have a wide array of styling options.