This urban combo of a crew-neck sweater and black ripped jeans is super versatile and apt for whatever adventure you may find yourself on. Feeling experimental? Switch things up by rocking a pair of black and white low top sneakers. Can you see how extremely easy it is to look stylish and stay comfy when fall arrives, all thanks to combinations like this? Guys who are curious how to pull off cool off-duty outfits well into your 30s, you have your answer.