There are few things better than a structured Gap jacket. I paired it with a striped blouse from the Gap also. I wore it with lighter combat boots to add a little color to my outfit but it could go great with a variety of different types of boots. What works about this outfit is that is warm, because even on the west coast it gets a little chilly from time to time. This makes a great wear to work look also, depending of course, on the attire allowed at your workplace.