Yes, always. I look at my pile of crap and put a number from $100 to $200 on it. Then our accountant says, "it was more like $350, wasn't it?".
I think it is definitely a Grey area.
An example:
Let's say you give a never-worn shirt with tags still attached to Goodwill, or something similar.
Tag reads $24.99; though Goodwill will obviously sell it for less than that.
It also could be a woven basket from Hobby Lobby with a tag of $24.99, or a light fixture from Lowe's.
How much do you think the IRS allow you to deduct for these types of $24.99 items??