We are using plank style siding rather than shingles.

Also... would you you keep or remove shutters?

I know they are ugly fake shutters... but I worry the windows are too far apart to have nothing on them.

Following.

Nice house! I like the current light siding with the brick, so maybe stick with something light. No shutters, especially on the 5 larger windows. I could see white or light, warm gray for the siding that can work well with your ( nice!)brick. Just wondering if black trim around the windows (instead of shutters) would be nice with your roof. Brick with white black can be very classic.

Here's one example with a color that looks similar to Hardie Cobble Stone. These windows have appropriately sized shutters. Each shutter should be half the window's width...a problem on double and even wider windows.

I agree about the shutters. Since your are residing, you could add a bit wider trim around the windows.

Boothbay is a very lovely color with your brick.

HardiePlank Boothbay & Evening Blue (New Providence, NJ) · More Info

Mountain Sage is also a good color with brick.

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Gray Slate would work.

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If you want to go lighter, Navajo Beige would look good.

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The Mountain Sage is a lovely color. That would be my pick.

Looks like you have shutter dogs, which indicates closeable shutters. However, they could never properly close over the double or triple windows. I would remove and live without them for a month or so and see if you can adjust. I think with the body of the house in a nice color you'll be able to manage without them. Larger window trim may be the answer if it still feels naked to you.

Any color would be good, except blues. Greens go good with red brick.

I vote for Cobble Stone

Green for siding, for trim, and no shutters: