Team a crew-neck t-shirt with brown jeans, if you prefer to dress for comfort without looking like a hobo to look stylish. On the shoe front, go for something on the more elegant end of the spectrum by slipping into charcoal leather chelsea boots. Keep this getup ready to go when spring comes, and rest assured, you'll save time getting dressed on more than one occasion. This getup illustrates how 30-year-old gentlemen score in the fashion department.