"In many ways, Hopper likes to hide and he doesn't want people to see the pain that he experiences every day and doesn't want people to see what he's feeling. So he has this big wide brim, a 3 inch rim that he can pull down and hide behind." David Harbour on Hopper's hat.

. ...

Jim Hopper grew up in a world where boys weren't supposed to cry. Not even when they fell off their bikes and took half the skin off their elbows. Not even when they sat in the high school parking lot while the love of their life was at the senior prom with someone else. Not even when their little girl, who had absorbed more pain than should ever possibly fit into such a tiny body, finally just stopped. Not even then. Which is why he found himself alone collapsing into the corner of a rarely used stairwell. In the world Jim Hopper grew up in, boys weren't supposed to cry, so when they did, they made damn sure they didn't have an audience.

The world didn't have the decency to even slow down for a damned minute so he could just get off, so he stayed on. He sheltered in place. He did what it took to wait out the rest of his time that he neither wanted nor deserved. And that time passed. And the pain remained, but it was less raw. Most of the time. And he built something that at least resembled a life. He went back home where life was easier. He took a position of authority that allowed him to force people to remain an arm's length away and to experience the illusion of control. However broken he was inside, outside he was charming when convenient, gruff when necessary and sharp witted always. He wore his uniform like armor and took to wearing his grandfather's hat like a shield, hiding his eyes when they threatened to give him away. And from time to time when he collapsed under the weight of it all, he made damn sure no one saw. That's what pills were for. And alcohol. And women. Because boys weren't supposed to cry.

The funny thing about purgatory though is that it's not intended to be a permanent destination. It's a place of pain and suffering just this side of Hell, but it's also a place of purification and redemption just this side of paradise. For Jim Hopper, the opportunity for purification came expertly disguised as his first missing person case since returning home: Will Byers.

He'd avoided children for years. Hated them, really, which is an objectively terrible thing to say. But it was too hard to feel the pain children who were not Sara inflicted on him, so he went with anger instead which was a far easier emotion to deal with. Boys weren't supposed to cry, but they could be angry. He also found it easier to be angry at Joyce Byres than to be hurt by her, so when she came to his office demanding that he look for her son, there was a small ugly part of him that was actually glad that she was experiencing some of the pain that had become his daily reality. Misery loves company, right?

He didn't want to look for Will Byers, but he did. And in looking for, not just one missing child, but two, hidden by layers of government conspiracies and shit he thought only happened in horror movies, Jim Hopper most unexpectedly found...himself. In all his glory and in all his shame. He stopped hiding from himself and confronted the demons that had kept him just this side of Hell for the last five years. Redemption was the way out of purgatory and the first step towards redemption is forgiveness. No one was more shocked than he by the revelation that he was a person worthy of forgiveness.

He'd avoided children for years, and so it was particularly surprising that this particular man stopped by the woods on a snowy evening to...to do what, exactly? To deliver a meal to someone he didn't even know was out there? To try to right a wrong that might be irreparable? To save one little girl in order to make up for the one he failed so completely?

He left the food in a wooden box. Reverently, almost as though it was an offering being laid at an alter. But really, it was more than just food. It was a lifeline he threw into the abyss. An attempt to show the only other soul more lost than he the way out of her own purgatory just this side of Hell. If she was out there, if she saw him, she didn't reach for the hand he extended.

Until she did.

Until hunger and desperation and maybe even a little bit of hope drove her to reveal herself to him.

He heard the noise behind him and stopped. Stopped walking, stopped breathing, and allowed himself to hope it was her and not just an animal. She placed herself before him, like an offering at an alter, risking everything for the chance at a way out of purgatory.

Before he could even close his mouth from the shock of it all, he pulled the hat from his head.

A/N. Go watch the first couple minutes of S2E3 and you'll see what I'm talking about. David Harbour has talked about the meaning of Hopper's hat in several interviews and so I rewatched his scenes looking at how that prop is used (because nothing in Stranger Things is an accident) and I was struck by this scene in particular.