Exactly
If you try too hard to be cool you just give the opposite effect.
It's not even that they're trying to be cool. It's that they, like Windows, are trying to stay backwards compatible with their origins in the 60s. Before the word cool even existed. So it's a mix of "the now" with "the then" (the music, a lot of the artwork, the Q and M characters who got older and older and then the actors passed away and were replaced with new actors who can't embody the same characters).
The James Bond brand is just too old to still be relevant.