Often used to gently point out someone's age-related hair loss. My uncle is getting quite thin on top now.
Pro Tip 2/3
Sensitive Topic
Be cautious, as mentioning someone is thin on top might be embarrassing or offensive. I didn't mention he was thin on top, to avoid hurting his feelings.
Pro Tip 3/3
Casual Expression
Use in informal contexts, it's not suitable for formal documents or discussions. At the reunion, they joked about all being thin on top.