I use an apparently rare and exotic dressing technique best described as "I'm wearing it, I don't care."
People are going to see what they see regardless of what I show, and no matter what people will pass judgement.
No matter what,. a lot of people are going to think you are doing it wrong---it makes them feel more right ... because they worry about stuff like"What will other people think?" I don't have time for all that.
I do recommend cycling shorts on their own or under baggies. I used to wear cargo shorts, and tolerated the flapping pockets Then one day I had the misfortune to get a dangling modifier caught between my thigh and the seat as I was pulling away from an intersection with a good bit of gusto. That created a rather unique (thankfully) and very powerful sensation which I determined I would never repeat.