I have been to the U of T bookstore several times and always walk away with the same impression: chaotic and overpriced. There seems to be no cogent organization in place and the staff are disinterested and unhelpful when dealing with customers. One feels like they are putting the staff out by daring to interrupt one of their (no doubt very important) conversations.
My wife is an alum of the University and we have popped in to buy a few items of apparel. It is typically way (and I mean way) overpriced. Example: a sweatshirt for a toddler - $40 plus 13% G.S.T.? Oh no, no, no!!!
TIP: They sometimes have sales but I have noticed that what it looks like is they run up a bunch of cheap t shirts and sweatshirts with U of T logos and put them on sale. You never see these "special" items on sale at other times. Occasionally, you can find a true sale item but it is rare.
I once found a shirt that was on clearance and the staff would not sell it because the price tag was torn and part of the bar code was missing. Despite the fact that every other piece of the tag was there along with the price, the staff member could not be bothered looking up the code or manually entering the price. One of the most absurd examples of bad customer service I have ever seen!
If you want a U of T shirt you are stuck with this place but don't get too excited beforehand, you will be disappointed!