Do you need crutches for a ligament sprained ankle?

Depends: On what grade or how severe the sprain is. If ligaments are torn i would use crutches.

Painful ankle: Possibly, but it would be best if you took it easy over the next couple of days. You can use price therapy. If the pain is still the same after 10-14 days you should see a doctor and get some xrays. Since you have had repeated sprains you would be best served by asking for a podiatry referral.