Hello Medic.
Sorry for the late reply.
My Shuffle survived its first run (10km). Basically, with my fanny pack around my waist, I clipped the Shuffle on to the left side of the fanny pack waistband, just above my hip, and using my own headphones, put the cable underneath my shirt and then over the top in to the Shuffle.
Really enjoyed running with it, hardly noticed it was there to be honest and it gives me less distractions as, with my Classic, I would sometimes skip through songs. With the Shuffle I just have to make sure the songs I take on my runs are what I want to listen to.
My Shuffle, as said, is slate (black), same as my Classic, but I think red looks good too. I really wanted orange (favourite colour) but they did not seem to offer that.
Thanks.
Ian