I'm like you with the matching. All of my ski gear (skis included) is black or gray. I just got a jacket that is a dusty blue, and all my base layers are odd colors, but basically I don't focus on matching.

With cycling, I've been saved because I don't have much money to spend on clothing. I tend to buy what's on sale, and if I matched my bike, I'd look lik ea barbie doll (my bike is teal and silver! ugh!). Right now most of my stuff is red, which doesn't really go with the bike, but I enjoy the disparity of the colors. I also have an orange shirt with pretty much clashes (in a good way) with the frame color.

The closest I've gotten to considering matching gear is that I do find myself tempted to buy a pink jersey, just because pink and teal is soooo Jem!