A trenchcoat and a denim shirt are indispensable sartorial weapons in any gent's wardrobe. Bring a more casual twist to an otherwise mostly dressed-up ensemble by slipping into black and white canvas high top sneakers. This outfit is everything for when leaves turn yellow and red and autumn takes over. Gents who are curious how to sport cool casual outfits as you step into your 30s, you have your answer.