Dress in a hoodie and khaki cargo pants to pull together a seriously sharp and off-duty outfit. Dial down this look with brown work boots. During winter, when practicality is imperative, it can be easy to settle for a less-than-stylish getup in the name of convenience. But this getup is a bright example that you can actually stay comfy and remain equally stylish during winter. Now that's an outfit any 20-year-old man will appreciate.