If I lived in Europe, or rode with a group, I would dress like the others. Sadly, I'm in the US, and mostly ride alone in places that don't see many bikers.
I too am in the US. I also ride solo 99.9% of the time (purposefully). Wearing bibs or bike shorts is something to get accustomed to for sure. My recent soreness exclusively prompted me to branch out into this attire, however, I am quickly learning the many good reasons to wear these cycling bottoms. I do not stop at the bar during/after my ride so I don't have to worry about that lol. I am also getting to an age where I couldn't give two poops about what anyone says/thinks about my look in any way/shape/form.
I am still not entirely comfortable with the 'look' but given the functional superiority.....I am quickly becoming a convert. On my typical rides I see many street riders out/about....and most are wearing full cycling clothing top to bottom. I don't plan to convert to full cult status.....but I do prefer my bits to be comfortable during my rides.
The padded underwear with cargo shorts sound like a reasonable plan to me.