I.W. Share definition Flag I.W. means being independently wealthy. i.e. having enough money to support one's self without ever having to work. Being I.W. in the New York dating scene is something women find very desirable in a man. I.W. by William Gilbert January 3, 2009 0 0 Get merch Get the I.W. mug. Buy Now โ $32.95 See more merch