I wear "street clothes" for most of my cycling. My average RT commute/errands/utility ride is 30 to 40 miles or so. Not always high intensity, but it adds up. And, I'm often rushing to an appointment.

In the past, I've commuted over pretty good hills, both in the city, and in the outskirts.

Once about 20 years ago I wore a paddle jacket (boating) as a commuter jacket. It seemed like a good idea at the time. Very water proof, head free, etc. Except I forgot about sweating... whew, that was bad.

Anyway, it really depends one's riding. If one is doing one block, then sure... wear it. If one is doing 20 miles... then there are much better jackets.