I have seen guys who have been on T for a couple years who still have a very noticeable dip in their waists. But fat does redistribute from the hips/butt to the middle. Working on the abdominal obliques can help straighten out the waist as well. Plus, as others have pointed out, the shoulder/hip ratio makes more difference when you are actually wearing clothes, and the shoulders do get broader on T, especially if you work out those outer shoulder muscles. (They'll get broader pre-T if you work them out as well, just not as quickly.)