A white hoodie and light blue jeans are absolute staples if you're planning an off-duty wardrobe that holds to the highest sartorial standards. Introduce white high top sneakers to the equation to infuse a dash of stylish casualness into this outfit. When you're having one of those bleak fall days, sometimes only a cool outfit like this one can cheer it up. Men who wonder how to wear cool off-duty dressing after thirty, you have your answer.