On your morning commute you have to be prepared for a curveball, especially when you're walking. When you have to sneak past the guy who lives in a dumpster, run from the neighborhood dog AND dodge your ex-girlfriend's building-weather is the last thing you need to worry about. Keep your head on a swivel and look good doing it.
Band of Outsiders Straight Leg Trouser ($240). Scotch & Soda Summer City Blazer ($80). Nylon Expandable Day Bag ($225). Jean Machine Shirt ($240). General Knot & Co Two-Tone Tie ($88). Jean Paul Gaultier Umbrella ($75). Open Ceremony Classic Boot ($295).