The series stars Bill Farmer with narration from Corey Burton and centers on Goofy as he is forced to stay in his home due to the COVID-19 pandemic.

During Fall 2020, animator Eric Goldberg pitched to Walt Disney Animation Studios chief creative officer Jennifer Lee and president Clark Spencer a series of shorts starring Goofy that centered on his life during the COVID-19 pandemic in the spirit of his How to... shorts, having been personally fond of the character.

[1][2] Lee and Spencer felt that Goofy's "everyman" persona was perfect to showcase regular life during the pandemic.

[1] Bill Farmer and Corey Burton reprise their roles from previous Disney media as Goofy and The Narrator.

[1] Goldberg choose to animate How to Wear a Mask due to the short's use of physical humor, which he always was personally fond of.