terminally hip
so incredibly laid back, disengaged, and lethargically uncaring and cool (usually in a contrived or studied way) that one is liable ultimately to die (literally expire) from lack of participation in one's own environment
Dirk is terminally hip: just look at him lying on the floor with his eyes shut during the dance, while all those women are flirting with him.
terminally hip
a person or thing or place that is very cool, hip and stylish, and unlike a wanna-be, is able to carry off the coolness with a natural and care-free elan.
Only the terminally hip get entry into Poison, Chelsea's newest night hot spot.