50 miles in non-padded shorts? Nope. Not for this guy. If the ride is long enough for me to wear a helmet and bike shoes, I'm wearing padded bibs.

Wearing a jersey is your choice. Personally, I prefer riding with clothing that isn't flappy, and is made from fabrics that help keep my body at a comfortable temperature. The rear pockets in a cycling jersey are also important to me (phone, tools, etc.)