This combo of a barn jacket and a charcoal crew-neck sweater is hard proof that a safe casual ensemble doesn't have to be boring. Want to go all out on the shoe front? Opt for a pair of burgundy leather derby shoes. As you can see here, this ensemble is a really great choice, especially for weird fall weather, when the mercury is starting to drop. More polished ensembles like this work well on 20-something gents.