“Should I wear glasses with astigmatism?”

If you have astigmatism, yes

My answer to you would be YES. If you have astigmatism, do you also have some associated nearsightedness or farsightedness? Depending upon how much astigmatism you have, do you feel safe to drive, especially at night? Are you seeing OK when working, when using a computer, or doing close work? Obviously, your safety on the road as well as the safety of other drivers cannot be understated. There are different vision requirements depending upon the state you live in, but safety should always be on everyone's mind. There are options as you mentioned including glasses, contact lenses, or refractive surgery. See your eye doctor in order to figure out what meets your personal, professional, and financial needs. Good luck and best wishes.

Depends on how bad astigmatism is.

If you get Toric lenses they will correct for astigmatism whether clear or tinted.