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20. Royce Leather 'Henry' Genuine Leather Legal Briefcase
You know how quickly a bag can turn into a black hole when it comes to your smaller knick-knacks, and this briefcase nixes that problem. Unzip the back compartment to reveal cred card slots, pen holders, a phone pocket, a binder, and a catch-all pocket. It's organization at its finest.

Royce Leather 'Henry' Genuine Leather Legal Briefcase, $329, Overstock