Frankly, there's something troubling with the idea that a major university needs to be a "brand" at all. The University of Michigan is in fact not a product generally available in the marketplace; the consumer can't buy a Michigan degree. One is admitted to Michigan by virtue of various combinations of effort, testing, etc. (including athletic effort). One then earns the degree.
Ultimately, it is the value of that degree that should be the "brand," but that's in an ideal world, where one would also want any items bearing the institution's symbols to reflect the value of that degree.
So in that world, maybe you'd have to have Armani or some other great designer create the school's football fan apparel.
However, reality is that very few people could buy it, and selling it wouldn't do the athletic department much good. So they license the symbols to mass-manufacturers of sporting goods like Adidas, and if that means obnoxious-looking trucker hats with the M logo, well, that kind of sucks but it is what we have for now.
Just for grins I went to the Harvard web store to see the kind of merch they're offering, and it's actually a lot more like the stuff that was available from Michigan suppliers in the 60s-70s; more traditional looking hats, Ts, sweats, etc.
So it is possible for a university to restrict the available offerings to more traditional (and some might say classy) things, but Brandon isn't going to be the guy to do that because rightly or wrongly he views his job to be raising as much money as possible, and not being very picky about the quality of the resulting image.