Go for a straightforward yet casually dapper option by marrying a grey sweatshirt and a long sleeve shirt. Wondering how to finish off your getup? Rock tobacco leather casual boots to spruce it up. During winter, when comfort is essential, it can be easy to settle for a less-than-stylish look. However, this look is hard proof that you can actually stay comfortable and remain equally stylish during winter. No doubt, a never-failing choice if we're talking dressing ideas for 20-year-olds.