Maybe we could add another play on words with "hot" meaning "sexy"...

Simple play on words
Cool = (literal) not hot = compliment
Don't look so hot = (figurative) look like crap = insult.

Well, in this form it's a really nice play on words. "You don't look so hot" could so easily be a compliment (as Mrs. Lindsay's remark was), if it didn't mean that the person looked awful! I wonder if she took it as one at first?

Based on an actual event. Mrs Lindsay (the mayor's wife) commented on Mr Berra's new uniform, and it was also a hot day. Different sources quote them differently, and not all sources contain the play on words.

This form is definitely not about looking good or bad only. Here comes the word play of cool versus hot meaning temperature. Yogi Berra's comment, therefore, can have two meanings "you look bad" or "you look cool too."

I think it's a play on words. "Cool" has taken on the meaning of "neat" or "good" from my days. "You look cool" would mean "you look good" (but also "cool" in the sense of not overheated). Whereas "not looking hot" definitely meant "looking poorly" (or, a

hot=sexy here! 100%

Yinyang philosophy at play, where Yin is darkness and Yang is brightness, and we can shift the domain to temperature from a light metaphor. But of course, gender must be taken into consideration in the dialog.

This is like when two old "friends" accidentally meet and falsely compliment each other while their real opinion is totally oposite. The woman is being false and Yogi is saying the truth.

Clearly, Yogi took cool for "you seem unhurried, serene" as the double meaning from "fresh or cold" and made a pun with the double meaning of "hot" for sexy instead of "more than warm". He told me!