I think you left out some context there.
Grace Hopper, one of the most accomplished computer scientists not just of her day but ever. Rose to dizzying heights in the US military because they needed her so much. A towering giant of the field. So when the picture of her comes up on screen, does the speaker say any of this? Does he acknowledge her greatness? No. He says she's wearing a cute hat. All her accomplishments and ability reduced to how she looks in a hat.
The problem here has absolutely nothing to do with the hat.