Consider wearing a beige crew-neck t-shirt and black ripped jeans, if you enjoy comfort dressing without looking like a hobo to look stylish. Let your sartorial skills really shine by finishing your outfit with a pair of slip-on sneakers. As the temperature lowers, you'll discover that an ensemble like this is ideal for the season. If you frequently wonder how to dress as a gentleman in his 20s, this getup is a real lifesaver.