Gone are the days when men had but one proven option for what to carry to the office: a briefcase. "The choice used to be black, brown, chestnut, leather, and you're done," says Tom Kalenderian, the executive vice-president for menswear at Barneys New York. That isn't the case in the Digital Age, when schlepping papers to and from work is no longer a workbag's primary function. The need to have computers, eReaders, smartphones, and iPods on your person at all times has given rise to an endless variety of dude satchels. That, and people have gotten into the habit of stuffing their lives in their bags. "We're cramming things in," says Kalenderian. This means the workplace is seeing more totes, backpacks, and shoulder bags than ever before.
With such a wide variety of man-bag features—from synthetic or natural materials to structured or stuff-it-all-in shapes to hard or soft shells—men are starting to learn bag language, something that women have long understood. "Now there's a level of choice above function and a bag's appropriateness," says Cuan Hanly, creative director and general manager at Jack Spade, the bag company that turned the messenger sack into a spiffy fashion item. "It's also about how you want the bag to speak about your character and your appearance." To that end, Bloomberg Businessweek tapped four experts—Kalenderian, Hanly, editorial stylist Michael Nash, and stylist and luxury brand consultant Kate Schelter—to translate what your man bag says about you.