Try pairing a long sleeve shirt with black jeans for a casual level of dress. And if you need to easily dial down this getup with a pair of shoes, why not add a pair of charcoal work boots to this look? Can you see how super easy it is to look dapper and stay toasty when chillier weather comes, thanks to this outfit? As you see, as a man in his twenties, you have a wide array of outfit options.