I think the best and safest way is to pick a color from the brick

If you are planning to keep the roof brown I would do something to go with it. I would go with the color the shutters are now. It looks really good on the brick. Then add color with the shutters. Burgundy or a deep red would be pretty. Love your landscaping and walkway. Looks like a warm and inviting home.

We're actually picking out shingles now - we're thinking a darker gray might work. I don't really love the red tint we have now. Our garage roof needs replaced, but we have a little more time on the house. So, we're going to try out the gray color on there and see how it looks with the brick.

I really like the look of the deep red on houses, but I was worried it would look too dark with our brick. I think I'll do a little Photoshopping and see how the red looks. Thanks so much for your advice!

Since you mentioned that you want to update...Please think about replacing the shutters with something else. These do not really go with what you are trying to do. The panel type would look updated and nice for your home.

Oh, we're definitely replacing the shutters. I don't like that look at all. We're in a small German town, so I think that's the look the previous owners were going for. If we did a dark red siding, what color of shutters would work well?

A deep charcoal blue grey to black would go with any new shingles you have picked out.

Do you NEEd to replace the siding or you just don't like it? I actually don't think it looks bad. I think new roof and new shutters in diferent color will go a long way.

We just don't really like the yellow. It's not in too bad of shape. There are some spots that could be replaced, but really it's that we want a new look for the house. I agree that the shutters and shingles will make a huge difference...maybe we'll do that first and then change up the siding afterwards if we feel it could still use a change. We just wanted to make sure we consider everything, since the shingles are something we have to fix now. If we're fixing one element, we wanted to make sure it worked well with any new things (like siding) that we change in the future.

Just make a painting/color plan. Where you want to end up eventually, and how to do it in steps. That way it will all go together.
By the way, there is paint for vinyl now. Since you are thinking of replacing it someday, you could try painting it first to see if you like the color or not. Someone in the one of the discussions painted her vinyl and it came out beautiful.

I had no idea that existed! Thanks for letting me know. That'd be a great way to save some money and not have so much pressure if it's not exactly what we wanted.

If you are handy with computers, i recommend you use photoshop to play around with the colors to see

This is a super rushed version, but I thought I'd upload anyways.

Oh, I think that looks really nice!! By the way, it really makes your landscaping stand out. I hadn't even noiced it before, I had to check back and see if it was there all along. Something about these colors makes them really look good. You did a beautiful job with the plantings!