16. The Boxy Briefcase — You saw it on the street-style blogs, you're seeing it here. It's the structured briefcase's time to shine. Not only does it look like you're killing it career-wise, these boxy numbers can fit your laptop and those important papers we know you're carrying around. No more messenger bags, okay?

Billy Kirk Schoolboy Satchel, $365, available at Need Supply; Salvatore Ferragamo Briefcase In Embossed Calfskin, $1900, available at Salvatore Ferragamo.