The phrase indicates a successful or advantageous position, often beyond expectations. After the court case, the defendant was sitting pretty.
Pro Tip 2/3
Casual Expression
It's a casual idiom, best used in informal conversations and not in formal writing. If we win this contract, we'll be sitting pretty.
Pro Tip 3/3
Often Financial
Frequently used to imply financial comfort or security, but not always about money. With those test scores, you're sitting pretty for college admissions.