Is that a messenger bag or are you just happy to see me?

Ben Sherman Leather Flap Messenger

This bag is for the upwardly mobile, goal oriented sort, who alternates between graduate school and an internship in the field. To be worn with a suit, black shirt with small white stripes, and no tie, but can also work with the cerulean v-neck sweater and Diesel jeans. Keeps your iPhone, iPod, and MacBook Air right where you need them at all times. And bonus points for walking or standing with your hands casually in your pockets while wearing the bag. Big, big bonus points.

$98, online only, urbanoutfitters.com