February 18, 2018 - Frazer Harrison/Getty Images North America more pics like this »
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11. Usher
Usher is the ultimate in "cool dads." No sandals and shorts for this handsome recording artist. He and his son Usher V (known as Cinco) looked dapper as all get out at the Gordon Parks Foundation Awards Gala.

Usher described his perfect day with his wife and children to People magazine: A hot air balloon ride over Italy. Sounds pretty magical to us.