This classic and casual pairing of a grey sweater vest and navy jeans is extremely easy to throw together without a second thought, helping you look on-trend and prepared for anything without spending a ton of time rummaging through your closet. When in doubt as to what to wear when it comes to shoes, go with a pair of brown leather brogue boots. So if you're after a kick-ass outfit that will take you from winter to spring, this is it. As a 30-year-old man, you want to start dressing more like a mature gentleman. If that's the case, getups like this are perfect as inspiration.