We found, last year, that most knit pants had plenty of stretch & didn't look odd. Fleece pants, especially those with sweatpant styling, have plenty of room. Hannah Andersson pants are great! And of course, knit longies are terrific. And most one-piece outfits are roomy through the trunk & accomadate diapers well. (Found some fleece jumpsuits at Costco last winter that were cute & warm & cheap!!)
Unless you have a long, thin baby, jeans may not work well over cloth diapers. BUT, if you can find capris in a "bigger" size, you might be able to wear them as regular-length pants over cloth. (We had one pair of embroidered denim capris--Land's End, I think--that were cute jeans last fall and winter but fit like cute capris this summer, when dd is longer & thinner.)
Compared to dressing ds (who wore sposies), I didn't really find it to be more difficult. All babies are different & clothing is cut so wildly different across manufacturers that it seems to always be a bit of trial and error.