A sweatshirt and navy skinny jeans are a modern casual combination that every sartorial-savvy gent should have in his casual lineup. If you need to easily kick up this look with one item, complement this outfit with dark brown suede chelsea boots. This is a fail-safe option for a killer outfit that will take you from winter to spring. Wondering how to perfect classic and casual outfits as you go through your 20s? This pairing is a wonderful example.