Funny vs. Concerning

Funny:
Grant came out of his room during resting time today wearing his winter hat and mittens.

Concerning:
His winter hat and mittens were in the back of the tall shelf in his closet. Waaaay out of his reach.

Funny:
The only other clothes he had on was his underwear. So winter hat, mittens, and underwear.

Concerning:
He doesn't have a stool in his room to assist him in being tall enough to reach the winter hat and mitten in the back of a tall shelf in his closet, way out of reach.