I spent my first 30+ years riding bikes in pretty much regular clothing. Then I discovered BF and a whole new world of gear, clothing and equipment that I had always thought were just for the pro racers. I have like 8 sets of bibs and I used to never ride without them, but over the last few years I have rediscovered the joy of riding in fairly normal clothing...albeit better suited for a bike than regular street clothes. Now for everything but roadie rides (where dressing differently tends to make the roadies shy away from letting you into their group because until you prove your skills with your legs, they are suspect if you are not dressed like the rest of the herd), I wear flat-seamed, gusseted-crotch undies and shorts made from wicking materials. The shorts are not skin tight, but far from baggy.

What I discovered is that I am actually even more comfortable dressed like this than I was in bibs...my "boys" have a bit more room to breath and my shorts and undies dry much faster than a chamois. Indeed, after many hot, humid summer miles, those chamois begin to feel like a wet, bacteria-infested diaper.

Of course a good, proper-sized and positioned saddle is a must, and you do need some miles to toughen up your nether regions (especially if you have been spoiled by spandex diapers).

Again, I don't mind cycling shorts/bibs and I still wear them from time-to-time, but this notion that they are some kind of requirement is simply not true. YMMV, of course.