And she says, "Your dog is So Cute" and I immediately think "So are you", but I don't say that, I just smile and keep walking. Is it creepy to say that out loud, or is that a perfect inroad to talk to them?
It is never a good idea to compliment a woman on her appearance. They will use it as a weapon against you. Even if you've known them a while just say, "You look okay." You can say nice things about their clothes or their shoes, but not them.