The San Francisco Chronicle lists the Rough Rider as the IN bag for "brogrammers"

The leather Rough Rider, the one Indiana Jones might wear were he transported to the 21st century, made its way onto the San Francisco Chronicle's list of status signifiers for the male tech community. 

"WHAT'S IN: Rustic, grown-up briefcases and shoulder bags by the likes of WaterField Designs, a local, timeless staple. And yes, WaterField even has backpacks for the stubbornly scholastic."

Of course, you don't have to be a "brogrammer" (or even male) to get satisfaction from this all-leather bag for decades. The Rough Rider's premium, full-grain, grizzly leather comes from the best (and most expensive) part of the hide. The leather's tight grain ensures that it will last forever. Over time, frequent contact will bring about a rich patina that is sure to create envy among your colleagues.

A built-in padded laptop compartment fits a MacBook Pro, Surface Book, Surface Pro, iPad Pro, and similarly-sized PC laptops. 

 

"The New Brogrammer Status Signifiers", Valerie Demicheva, August 10, 2018, San Francisco Chronicle