Ironically, cool. (Not “ironically cool” … ironically.)
“Funny” T-shirts?
Possibly funny, depending on the joke.
SUVs?
NOT cool!
Liberty Mutual tv ads?
Not Cool.
CATS the musical?
Not cool
Leopard seals
Cool
Navy Seals?
Definitely Cool
People who read actual booka
Cool as can be. 
Taylor Swift, late-2019 edition?
Trying too hard, was cool when she was country
B&W movies?
Cool in the color age
fedoras
Fedoras? Cool. (Calling a Trilby a fedora, not cool.)
Déjà vü? (The mental phenomenon, not the CSN&Y album.)
I feel like this was already asked. 
Cool.
Free breakfast sandwich at work.
Cool (unless you’re the one that has to make them of course)
The Greg Kihn Band
In the '80s? Cool. At the County Fair next week? Not cool.
American Graffiti?
Used to be cool, but now a relic, so not cool.
Charles Shackleford
Never heard of him, so by definition, not cool.
Boris Johnson.
Not cool. Uncomfortably dampish warm, even.
Kate McKinnon
Intermittently cool.
Tina Fey.
Coolissima!
Samantha Bee?
Meh. Not so cool.
John Oliver.