For an outfit that's very easy but can be dressed up or down in a variety of different ways, go for a bomber jacket and a black shirt jacket. When in doubt about the footwear, go with a pair of charcoal leather brogue boots. When it comes to dressing for transeasonal weather, nothing beats a neat combination that will keep you toasty and looking your best. Men wondering how to rock cool casual outfits after 30, you have your answer.