Pairing a hoodie with tobacco chinos is a good choice for a cool and casual look. If not sure about what to wear when it comes to footwear, go with a pair of white and black leather low top sneakers. As you can see, this look is a really smart option, especially for transeasonal weather, when the temps are starting to drop. The ability to pull off getups like this is one of the perks of being middle-aged.