If you feel more confident in practical clothes, you'll like this casual combination of a beige biker jacket and black jeans. Finishing off with a pair of grey suede chelsea boots is the simplest way to add some extra fanciness to your getup. It's a smart choice when it comes to figuring out a neat outfit for awkward fall weather. This outfit illustrates that as a 30-something man, you have a wide range of outfit options.