Boots in some type of redish brown would look good, I think. The length of the sleeves is probably supposed to be long, so I'm not sure you would need to have them shortened. I think I'm at the age, though, where I think shirts that are not tucked in under jackets looks sloppy.
I won't say they're annoying, but most of the time you can only see the top half. Does Style Forum have a "share your music" type thread? If not, why not create one? Seems as if you're more interested in sharing your music.
I think maybe he's implying PG is more into the look and romance of being a cyclist. Of wearing the gear, the cap with the brim turned up, the fancy bike, imagining himself in the Tour de France. I'm not saying that's what PG is doing, but he does seem to have dove right into it.