I'm aware that the instinctive answer will likely be no. However, I commute 28 miles a day, and generally just wear boxers.
I get a little bit of skin irritation once and a while. But no less than I did when I wore bike shorts.
Recently, I did a few rides with padded bike shorts (I own several pair) and it just didn't seem real comfortable.
The longest I've ridden in one stretch in ordinary "civilian clothes" was 35 miles.
One compromise I was thinking was to carry a pair of bike shorts, and change into them if the ordinary shorts became uncomfortable.
Would chamois cream work with regular shorts?