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Though he hasn’t been in the workplace for long, 26-year-old Miguel Osio has already seen it undergo a strange transformation. Men—businessmen—are carrying backpacks, not briefcases. The New York-based marketing consultant has been startled both by the sheer number of toters as well as their demographic range. “I even see a few older guys, men in their 50s and 60s, commuting, getting off the subway in their suits and ties with their black Tumi backpacks,” said Mr. Osio, who carries a brown Tumi backpack himself. A briefcase, he mused, used to confer legitimacy on its owner, but that staid symbol of corporate success…