I bought these jeans from the Ross on the same strip mall as my Homegoods the other day, and I was absolutely in love with them-ignore shoe color. They are Calvin Klein blue frost jeans, which really has little meaning to me, but they were just awesome. The break in the pant seemed adequate to me, not too little or too much. But here's the problem, as can be seen in the second image, the top of the pants were low. In the image, where the bottom of the shirt sits is essentially where the top of the pant rose.
If I had the urge to tuck in my shirt it would look goofily low, and if I decided that I should raise my pants, then the break in the pant would have disappeared and major flooding would have happened.
I debated whether to keep them and deal with my insecurity, or to return them.
The final decision came with some advice from my roomie Andrew. He mentioned that if I felt comfortable and liked them then I should keep them. He told me that they looked fine, which is an opinion I was holding myself, but I just didn't feel right in those pants.
So I did what needed to be done, and I returned those pants...I feel that I made the right decision. Thank you Michael M. for your insight on fashion and your suggestions on fashion blogs and such. It helped in my decision to make the right decision.