1. You don't look good, but it's rude to tell you so.
2. You look good. (Possible)
Situation: someone has on out of style/season clothing and/Or jacked weave or hairstyle.. shoes, bag etc. You want to be nice but not lie.
"Haven't seen you in a while, look at you, looking like you're looking"
"You look good, over there looking like you're looking" (possible)