What is the positive connotation of silly?

Zany is a positive connotation of silly, but there are many depending on what definition of silly you're using.

Zany: adjective ( -nier , -niest )amusingly unconventional and idiosyncratic : zany humor. Zany: nounan erratic or eccentric person.• historical a comic performer partnering a clown, whom he imitated in an amusing way.