Gaf makes a weathered wood shingle, which is probably the closest you are going to get to your inspiration picture. I agree with millworkman, those on the inspriration picture are real cedar

I agree! $$ We cannot afford it or the synthetic cedar shake. I'm just trying to find the closest color match. Thanks so much for the input! If there is a different shingle brand that would better match feel free to suggest!

Would gaf shakewood shingles be too orange? I liked the look of them against our white siding in person, but the pictures I see online look orange in color.

Get actual sample boards and then after narrowing it down have thje roofer pick up a bundle of the two final choices and lay them out on the actual roof. Do not use a computer monitor to make your final decision or even a sample board.

Look at TruDefiniton Duration by Owens Corning. Sand Castle is tan and Driftwood is a tan, sage, grey mix.

The manufacturer or local distributor of the shingle you are considering will have a list of local customers who have used the colors you are considering. They will give you a list with addresses and shingle colors used, and you can then drive by and look at it on an actual house.

Hopefully you aren't in an area with gated communities! I am, but I still managed to get into several gated neighborhoods by having a hard copy of the email/lists from the manufacturer/distributor and explaining what I wanted to do. Also offered to leave my ID at the gate.

Doing these drive-by's is the only way to pick a shingle. Some colors looked fine as a small sample, but were hideous once they covered a whole roof.

Thanks. We do not have to worry about gated communities so that is definitely a convenience. Most homes with white siding have gray or black shingles in our area (a few of the new builds are going for the modern farmhouse aesthetic). I don't like the look of a cool toned roof and siding for our home as it is a dutch colonial and I want to incorporate warmer accents (wood shutters and copper or faux copper gutters). I'm concerned if it is too cool toned, we will forever be stuck with black/dark shutters. You're right, the wrong color shingle would be a disaster as it would encompass our entire second story. Thanks for your input! I will make some calls and see if I can get some info!

I would get a couple samples of the shakewood, and also the weathered wood. Thats the only way you will know. The shakewood, does appear in pictures of having a bit of orange. Lay the shingles up on your roof, so you can view them, on your house. I would want at least 6 of each to lay out, so you get the true picture.