I felt the same way as OP a long time ago, but then I changed.
Where I live, the ground/streets/sidewalks are really dusty during spring, so if I skate I'll get tons of dust on my grip by the time I get to the spot or park. Not trying to grip gum my board at the spot either, that'll take precious time away from the session.
Currently I've been walking with my board to a park that's about ten minutes away. If I skated there, my board would be full of dust/slippery and make for a garbage session.
It's also pretty flat in my neighbourhood and the ground's rough, so that combined with the dust doesn't make it that much fun of a cruise. Plus I find that simply walking is a good way to warm up my legs for the session.
I also bike to some parks and use a bag for my board, similar to what arrbee posted. It's a bit laborious and uncomfortable but it also saves me time.
At this point I don't care what's cool and what's not cool, if I like it I'll do it.