No, you don’t have to wear a mask all the time, every time you go outside.
The guidelines are well-established at this point. You are being asked to wear a mask whenever you cannot maintain social/physical distancing of at least six feet. The pandemic is a medical issue, not a political one. Follow the science and advice of the public health authorities. The current upsurge in COVID-19 cases through the states, such as California, Texas, Arizona, and Florida, despite advice against it or concerns over it, is proof that this pandemic is far from over.