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Meaning

looking better by night, from afar, or under a hat

Seen at night, from far away, or with the face partly hidden under a hat, a person looks more beautiful than they really are because the details cannot be made out. Said mainly of women.

Example

夜目遠目笠の内というとおり、写真の印象と実物はかなり違った。

As the saying about night, distance, and hats goes, the person in real life was quite different from the impression the photos gave.

Origin

Yome tōme (seen at night, seen from afar) on its own means only that things look blurry. Adding kasa no uchi (under a hat) makes it about people, especially women's looks. Some take kasa to mean an umbrella or parasol. An example appears in the early Edo haikai collection Enokoshū (1633).

Sources