Medium gray is usually a good choice for roof color. With brick sage green is an attractive siding color with a shade daker for trim.

I copied and linked to some possible color palettes. I'm in the process of choosing the roof style and color, then will go from there. I'll post "before and after" photo but it will be a while. Like months and months, as I am just starting to get quotes.

Edited to add that the links for some reason didn't show up . . . now I can't find them, but the photos in my original post are sort of the same kind of thing . . .

I was thinking you should do something like cedar shake shingles if you really want to give your house a cottage vibe, and then i noticed most of your inspiration photos have cedar shake roofs. Obviously cedar shakes aren’t cheap, but it might be worth checking out whether there are any cedar shake alternatives out there (ie synthetic options that would give you the look of cedar shakes) to see if there are any that might fit your budget.

Yes, looking for a modified cedar shake look, like a greyed brown which is the color cedar gets when it's weathered. Once we get the roof style nailed down, we'll pick our other colors from there. I like the idea of switching out the garage light fixtures too, I've always disliked those, although enviro-frugal me might end up just spray painting them . . . Right now I'm thinking I might try to match the putty color between the brick for the garage doors and siding. I don't want dark brown blobs, since my house is actually very "garage forward." But dark bronze trim would make the lights and windows pop, but in the opposite way they pop now! There's a bay window hidden by shrubs that will eventually get exposed when I cut down the shrubs and it will look good with dark bronze trim. Here's the only other photo I have right now showing the front, including the big white blob garage doors. It's actually a photo showing off my pepper harvest, but that's all I've got. I just want something warmer that isn't as "contrasting" but doesn't clash. That's harder than it seems when it comes to mixing colors with brick. Grey as a high contrast is lots easier than matching brick tones without clashing.

Wood-look garage doors with bigger windows would be nice, but given all the other expenses I'm shelling out for, totally replacing the doors with something expensive would have to wait. We are also redoing our back porch to enclose it and install a wood stove.

Hoping for a redo with colors more like this . . .

Boy this is proving to be tough!! You absolutely need to see the actual shingles to make sure the colors match with the brick to give the effect you want! It's not a no-brainer with complimentary colors and brick, so many undertones and each brick house is unique. The online tools are kind of worthless since what is on the monitor is almost impossible to gauge as far as the undertones and local light conditions. Most of the local roofing guys do not have samples! :(

Our roofing contractor got us large pieces of the colors we were considering. We put them on the roof for several days to help us decide.

@ I pinkmountain I have no help, but can offer my sympathies. Picking a siding/trim color for our brick house was the hardest paint decision I’ve ever had to make. Still not sure I got it “right” but happy to finally have something I can live with. Hang in there!

Well, I finally was able to make a decision. I looked at the fake shake styles and also fake slate tile styles and I just didn't like the quality or the colors. Not enough to justify the large extra expense. After trying a gazillion mottled shingles that I guess were supposed to emulate weathered wood, I decided to go with a medium brown overall, not mottled. I felt that the mottled colors competed with my very mottled brick for attention since my house is half roof. I'm hoping a more solid colored medium tone roof will draw attention to the brick. Gonna wait on a siding redo. We are redoing the screened in porch and adding a wood stove also this year so gonna wait on a garage door/siding/trim redo until next summer. The shingles I chose will not fight with the white for now but look even better if we eventually go for more earth tones.

I will post "before and after" but it will be a while. Just so happy the shopping and hemming and hawing is over for now!

You seem to want something that pops! Here's a scheme that works well with your bricks.