Thanks Buffet girl! Very helpful. Yes, our siding is kind of creamy yellow but definitely reads yellow.

I am stuck on lighter vs. darker gray. I need to also drive around to figure out what the Timberline Weathered Wood shingle looks like. Online it looks like maybe a mix of brown and gray. I have samples here but that isn't incredibly helpful IMO.

I have weathered wood shingles on my house and they read more brown/beige than gray. I think that with the yellow roof, a more definite gray would be better and would look very pretty. Is there a medium gray?

Timberline Oyster Gray is another option. I think that's more medium toned gray, and I think I'm leaning that way. I think ;)

My neighbor has a 2 story victorian that's yellow with white trim. She just changed from a brown roof like yours to a blue roof and blue shutters; looks nice.

Our house is a yellow/creme color with green shutters, we went with a medium charcoal gray and are very happy with the look.

When you drive around, notice how contrasting roofs (dark roof/light siding & vice versa) look good on some houses and make others look chopped up & squat. Roof color depends on how prominent the roof is & if you want to accentuate it or not.

Take some pictures of your house and color in a dark roof versus a medium color or a light color. That helps a lot. Or post the picture here & maybe someone can photoshop the picture for you.

Well, it is very similar to the house in the OP. Basically a simple roof line, typical colonial, no overhang over the porch. Very simple lines overall.

The contractor said "slate" is the most "gray gray" but the sample has lots of green flecks (I don't think it would work). Oyster Gray is not readily available. It is "less blue" than pewter. THe pewter looks very dark to me though. This is hard!

It is hard. When we got our roof done in 2007, the roofing company gave us a list 3 pages long of roofs they had done with the same Certainteed brand of roofing we wanted. We drove around for 2 days looking at the different colors to figure out which one we wanted. Up close ours has a slight undertone of brown but from the road, you don't see it and from the road it is a soft medium charcoal(ish) gray.

It is fascinating because I've noticed the flecks can be rather prominent, or fade away completely. I have neighbors with a brick home/blue siding, and they have very small blue/red flecks in their shingles. It works with their home, but you can absolutely notice those flecks. I know one of the shingles we saw has flecks of multiple colors and yet they sort of blend and fade away when seen from the road. He gave us some homes to look at but I still am struggling because I do think his suggested gray (pewter) is a little darker than I'd prefer. We have until monday to pick a shingle color, so I expect to be driving around and looking at a lot of roofs this weekend. I'm starting to wonder if the GAF/Timberline has the right color for me.

We got our roof done in 2007 and used Certainteed. I'm having a hard time recalling the color we had installed by name but I believe it was either

Colonial Slate:

or Weathered Wood:

Weathered Wood definitely has more brown in the mix and it can be seen more from the street but neither were too dark from the road which is what my biggest concern was. I'll try to find out which one we used and get a picture for you later today.

THanks Lukkiirish. I like weathered wood in the larger sample size but I'm afraid it will read too "brown" from the street. I need to drive by a home with it and take a more extensive look. Our current roof (from previous owner) has a little brown in it and it looks fine so it may be an option. I like that the WW has a less harsh/dark feel. Just not sure about the brown vs. gray.

The big 2 story farmhouse up the road put in new pale yellow siding and their roof color is a medium brown. It's just stunning. No blue though, but the medium brown is the perfect contrast.

Looking at your link, the last post w/pics, I like the second from top pic. Looks to be a medium gray. I think shingles are so hard to pick because the house style and lighting make so much difference. We just went thru this and the driving around helped us make a decision. Good luck!

I think the first question is are you planning to always have blue shutters (or perhaps a grey or black)? If so, you might prefer the grey shingles.

If there is a chance that down the line you would want to switch to a green shutter or white, or even a brown/black, then I think I would choose the Weathered Wood. That is what we have on our house,and while it is in the brown family, it has a lot of grey in it.

Thanks Les. We've considered going w/ a greener or more sagey type shingle down the road but I'd say that's not super likely overall. We also have a red door. Not sure if that sways things in any way.
Contractor dug up a sample of oyster gray (timberline 3-d) today (well, a "bigger" sample where you can see several shingles. To my eye it looks less dark than pewter (which I still think is a little too dark?) and fox hollow (which on the sample board looks a little too light). Yet he said it is not a popular color at all and would require going somewhere else to stock it.
I still think pewter seems too dark but the roofing guy seems to like that or the weathered wood. I'm having trouble finding many exterior images of yellow siding with visible roof colors.

I always prefer a dark charcoal. Good luck!

Ok, well I don't know if this will help or not. We live on a hill and the roof doesn't seem to show much from the road. Sorry. After looking at it though, I believe we went with Colonial Slate. Excuse the mess, other than the roof, we haven't worked on our exterior at all. :c(

I wish I could find an equivalent in the GAF Timberline. I like that color. I can't find too many "medium gray" options.

Can you post the link to the color options you have?

Certainly!
IRL slate has green flecks to it. My samples (larger ones where they have a few real shingles on a board vs. a tiny sliver) look as if fox hollow is way too light. Pewter looks too dark to my eye. Oyster Gray is supposedly "less blue" than Pewter. Pewter has flecks that are just slightly blue to them but it is not easy to detect. To me, it looks like on the samples I have that Fox Hollow has lots of the light colored flecks, oyster has a medium amount, and some of those same light flecks are on pewter but it is much darker. But apparently Oyster is really not a popular option and would require a trip to another place to buy the shingles vs. Home Depot. The only other one I kind of like is weathered wood.

THere's a house down the road with yellow siding and a darker (like pewter I think) roof and I'm not super wild about it. It is a colonial, but has a wrap around porch so more visible roof, which might be part of it I guess. My colonial has simple rooflines, no porch overhang (no lower roof on main part of the house). I have a 2 car garage out the back of the house (drive around to it) and have a room off the side of the house visible from the street (a vaulted ceiling family room).

Here is a link that might be useful: shingle options-timberline 3d

Well the oyster gray didn't come up on my computer because they only show what's available in my zip code but if you like the color and feel it will work well your house, you shouldn't concern yourself too much about whether it's popular or not. As long as the finished product looks the way you envision it to look and it conforms well with the homes around you, you should do what you want. I would also not really concern myself with the specs of color in them either because from the road or even the ground, they really won't show. Up close our shingles have brown undertones and some other colors but it really didn't make a difference.

I believe that slate is the closest match to ours. If you're going to keep those blue shutters it would be a nice compliment, better than the brown IMHO.

We drove around today and I think I'm leaning toward weathered wood for now. I hate these decisions.

My siding is really more cream, but reads a little more yellow because of the blue shutters. It is very similar to the color combo on the shed linked to below.

Here is a link that might be useful: shed w/ similar color scheme-cream/blue

Sometimes the monitors mess up the colors and we don't see the same thing. I'm sure it will look lovely, I love the way the two tones look in your sample picture.

I hated making that decision too. It was a toughy but once it was up, we were really glad we took the time needed to do what we needed to do to get it right. You will be too! Don't forget to post pictures when it's done!