In the absence of very specific context, I would find it creepy and condescending coming from a man I don't know well -- so, in general, only if it's said as a joke by a male friend, would I find it okay.

Coming from a T, the creepiness + condescension factor would be off the charts.

Then again, my boundaries about these things may be far more rigid than other folks (having grown up in a culture where men making public, graphic comments about women's and girls bodies was the norm, I am rather sensitive to it).