For a casual menswear style with an urban twist, you can easily dress in a black crew-neck t-shirt and charcoal ripped jeans. Let your sartorial credentials truly shine by finishing your outfit with grey canvas high top sneakers. When it comes to dressing for transitional weather, nothing beats a kick-ass outfit that will keep you comfy and looking your best. This combination should encourage anyone who wasn't sure about sporting casual outfits as a mature guy.