The early days of fall, when you can still get by in an unlined jacket and no socks without feeling like Jack Nicholson at the end of The Shining, are few and fleeting, so take advantage of the weather while it's still cooperating. A simple black t-shirt pairs well with sturdy cotton trousers in a fall-favorite light brown while the loafers let the world know you mean business. A versatile, neutral bomber serves you well in just about any situation you send its way, and looks just as good thrown over your shoulder during the midday sun as it does when you first put it on in the morning.
Jacket: Michael Kors
Loafers: 14th & Union