1. A kitten or cat that wins at life.
2. The act of helping others and/or doing awesome unto others.
WinKitty was a word founded by a user named "meekakitty" on YouTube. It was popularized by John Green of the Vlogbrothers, when he asked his many subscribers what "WinKitty" could possibly mean.
1. Jingles is very WinKitty!
2. The Vlog Brothers, Hank and John Green, do various acts of WinKitty on their YouTube channel.