I'm 5'10" and weigh 320. I ride a 88/89 Schwinn Voyageur with a brooks b-17 as my commuter bike. So far the only thing that is comfortable to ride in are bib shorts. I don't mind this when I'm just going for a ride, but when I commute I'd love to not have to change. Especially the two days I attend classes (college campus), or when I shop with my bike. I've tried compression shorts under cargo shorts. This is okay, but I seem to miss the bib's padding. I've tried bibs under shorts and this doesn't work. Especially after walking around campus and then returning to the bike. The "fellas" tend to shift and getting everything to line up isn't easy.
So my questions:
Given my experience with bibs under shorts is it worth the financial investment to try a mountain bike short that has a liner sewn into a regular short or will this just feel like the bibs under regular shorts?
Would a more modern padded saddle be a better choice for commuting in compression shorts under regular shorts?
Oh and I do sometimes just ride in regular street clothes. This isn't awesome either.