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I notice that skinny can either have a negative or positive or neutral connotation, but fat seems almost always negatively used (ie. I have almost never heard anyone use fat in a positive way, at least on this continent!).
I still remember when I was a kid in grade school, at one time I got scolded by a teacher once for saying someone was fat but didn't get the same response when I said someone was skinny (even when I tried to use either without malicious intent -- as a kid, for instance, saying "Which one is Joe?" "The fat boy or the skinny boy?"). But hey, I learned about language usage and the hidden meanings people attach to words that day.
Either way though, I usually don't really care to comment on someone's body mass in general.
I used to have people comment on how skinny I was as a form of meaness. People would watch every bite I took, and comment---no wonder you're so skinny! Look at how little you eat. Then they would heap more and more food on my plate, oh, you need more food, you're sooooooo skinny.
What bugged me most was they would hold up their thumb and forefinger in a tiny circle and say oh, look at your poor little matchstick arms! BTW, I was NOT skinny---I was 5"5'and 120 lb,. slender, not "skinny".
How I got back was by giving it back. Oh, look how fat you are! No wonder you're so fat, look at all you eat! Then hold both arms open round and say, oh, look at your big, big butt! When told I was being rude, I said oh, how 'bout that?
Somebody once told me I look like something out of Belsen. Extremely rude of them, and we're not allowed to go around saying "You're looking fat today" are we. Double standards.
I would never tell anyone they looked skinny no matter what. To me, skinny means "too thin." Also, as one poster pointed out, you never know if someone has a disease and are just plain ill. I almost died of bacterial dysentery on a medical mission in a very poor country, spent three days in the capital crawling to the bathroom with a blood pressure of 80/40 despite constant fluids. Got back to the group when able (most of the group girls in their 20s) and one said, "At least you lost some weight." Thanks a bunch.
A couple of morbidly obese co-workers of mine lost a lot of weight in the year where I didn't see them. One did Weight Watchers and one had gastric bypass. The way I acknowledged the huge change was to say, "You're looking well, I haven't seen you in so long," and they were both eager to tell me how they came to be looking well.
I agree that commenting on anyone's weight, especially woman to woman, is rude. It's just too loaded. If you think someone looks good, maybe compliment them on their haircut or something.
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