You don't have to replace cool glasses with cheap glasses. When you buy a pair of glasses you get a blue case to keep them in. Actually, the case just takes up an inventory slot. If you buy a lot of eyeglasses you can sell the extra cases to the store, but hang on to one case. To remove eyeglasses drop the case onto the mayor or peep wearing the glasses. It may take a couple of tries. If it fails, the case drops to the ground at the mayor's feet (even if you're trying to remove glasses from a peep on the other side of town) and the mayor can pick it up.