mostly I ride sans-chamois. if I bike to work it doesn't dry out in time. touring i could be in bike shorts all day, so again i don't like the clamy-chamois.
I'll usually try to dress appropriate to the group - so if my friends are on road bikes in full super hero regalia, i'll do that also. And I just got a new-ish Brooks seat I'm breaking, so I'm opting for padding for the first few hundred miles.
You might want to consider recumbent shorts - compression shorts basically - bike shorts with no padding. Should cut down on chaffing you get with gym shorts. Or exposing yourself as your baggy gym short creep up and get lifted by the wind.....
https://www.aerotechdesigns.com/compression-shorts.html
-- These guys are great. I was after a set of chamois-less knickers, not the baggy pedal pushers, but tights - and these guys pulled two off the assembly line before putting the chamois in. Just really nice of them to do a special order at no extra handling fees.
That's a great idea, thanks. Sometimes I wear boxer briefs under the gym shorts, but have not considered the compression shorts.