I would never judge anyone for wearing tassel loafers, but I can't see myself owning a pair. I find them to be quite 'dandy'. I like the way penny loafers look on the shelf, but every time I've tried on a pair I've thought they looked rather odd on my feet. Maybe I'll go the monk strap route for a no-lace shoe instead. Though, the simplicity of slipping into the Hillsborough was appealing...especially when it's raining, due to the rubber sole.
Has AE ever made a wholecut loafer? Something like this...
They have the Ann Arbor on the clearance list currently, but it has a cemented sole.
Not exactly like that, but the discontinued model, Astor, is a wholecut tassel loafer.