Hard to do when you're plugging into the back of a workstation that's located under your desk. Or in a lot of other situations really.
Orient that seam downwards or (if the ports are vertical) to the right, and most of the time it'll fit first go.
I have come across a few setups that had a USB port 'upside down', but mostly this is on laptops where they've got the connector board fitted upside-down inside the chassis.