Using 'unhip' suggests awareness of social trends, but an outside position or lack of participation. Despite trying to be cool, his unhip choice of music was obvious.
Pro Tip 2/3
Self Awareness
When used to describe oneself, it indicates a humble or self-deprecating tone. I'm a bit unhip with the latest slang, honestly.
Pro Tip 3/3
Cultural Reference
Understand cultural context, as 'unhip' refers to what's currently unfashionable within a specific group. In this tech-savvy crowd, using a flip phone is considered unhip.