Our house is a light yellow cream color. I personally like living in a yellow house because it reminds me of a Blind Melon song that also reminds me about homeschooling with my boys. Click Here to hear the song. My husband likes that we live in a yellow house because its his favorite color. We most likely will always keep the house yellow if we upgrade the siding.
Our existing roof is very worn. It was a light brown, reddish color I think, but its so worn its difficult to tell.
At one point I thought a blue roof would be fun, kind of Swedish actually. My husband liked the idea of a green roof with the yellow siding. There are other yellow houses in the neighborhood with green roofs that don't look so hot. I worried about how a colored roof would hold up. Eventually that dye in the shingle will fade from the elements.
I know I didn't want black, but I didn't want to go too light either. A black roof would get too hot in the summer and since snow covers our roof in the winter, it wouldn't help during that season either. Light roofs don't look too attractive to me though.
We decided to try and stay in the gray family, but you wouldn't believe how many different shades of gray there are! We've gone back and forth for weeks now, but I think we've finally found our roof color.
I present to you..... Georgetown Gray. When I look at it closely, I can pick up shades of slate and sage.

I hope it works out, but I suppose until its up there on the roof, we really won't know. There are no other houses in the neighborhood with this roof as far as we can tell, so we're taking a risk, but then again, I like having something different than everyone else. Our subdivision is very cookie cutter.
This is not a photo of my house of course, (I wish!) This is the photo from the shingle manufacturer's website.
Someday I would love to add stone detail to the front of our house. All of the newer homes built in the cornfield next to us have a certain percentage of brick or stone along with siding. If we add this detail, it could help our home blend between the two developments.
I'll be sure to take a photo after the roof is on and you can tell me what you think.