This pairing of a charcoal wool long sleeve shirt and black chinos is hard proof that a safe off-duty outfit can still look really interesting. You know how to smarten up this look: black leather derby shoes. So when summer is fading away and fall is in the air, this outfit is likely to become your go-to. As you're moving from your 20s to your 30s, you want to start dressing like an adult man. If that's the case, inspiration like this comes in very useful.