I to wear my pants lose fitting and no not to my A@@ Crack. I have caried IWB and OWB and the only thing is that you will need to do is ensure you have a good belt that is a few inches larger. And depending on what holster you go with will depend on the comfort as well. My Super Tuck fits better and not as tight as my High Noon IWB. The Super Tuck is probably the best fitting holster I've ever worn. I only use my High Noon when I am appendix carrying. So if your wearing rock star tight jeans then you may have a problem but that would be the only reason I see for having to buy new clothes.
NRA Certified Instructor
US Army Retired
Prior Federal Police Officer Instructor