I adore this style. I know it has been going on for awhile now on the fashion forums and seems to come in and out of style every couple years. I have been wearing super baggy vintage 501's and LOOOOVE it!!! I am wearing them now!!
Super comfy and easy to wear when you are running around. How can you go wrong. Though I am not a fan of Katie holmes either I think she looks fine. The pin roll is a bit much but I still think with her choice in shoes and tops she is pulling it off well.