If you're planning for a sartorial situation where comfort is essential, this combination of a sweatshirt and dark brown chinos is a no-brainer. Now all you need is a good pair of brown low top sneakers to round off your ensemble. When it comes to dressing for unpredictable fall weather, nothing beats a kick-ass getup that transitions easily between seasons. This combination illustrates that well into your 40s you still have a wide range of sartorial options.