Image by david drexler, used under a CC license.
If anything, “Willis Tower” sounds more dignified than “Sears Tower”, mostly because we don’t associate the name with a large retailer. I don’t get too inspired by corporate naming (MCI Arena or Enron stadium are examples that come to mind). It’s very honest, I suppose, highlighting the fact that only large business concerns can afford to own massive structures. But it leaves something to be desired in the “sense of wonder” department.
At least with “Willis Tower”, I can pretend that it’s named after some great historical figure, deep thinker or artist. The fact that they’re really an international insurance broker can just fade gracefully away. Hmmm, delicious denial.