I'd prob go w/something darker in the charcoal family. I wouldn't do a putty color that matches the stone. that's blah.

The colors you've sampled look like pastel chalk colors. You're getting a good quality wood deck paint, yes? make sure you apply the proper primer.

(In fact, try priming the wood first and then put on your sample colors. what's happening is the paint is being absorbed into the wood and giving you skewed colors. )

you need some contrast.

you could also try something like these colors (just a putty color and white) but use a stencil so that it stands out. this would be cool looking. Try Cutting Edge Stencils. lots of choices. make sure to use the proper deck paint

That's super helpful - I think we're wary of a design painted down because we currently have an outdoor rug that has a pattern.

But for whatever reason we didn't even consider going darker - I think we were worried it'd clash too much with so much white.

And yes, I'm going to sand off all the chippy parts, prime it all, and then paint with deck paint.

Additionally, if we chose such a color as you suggested, would you suggest painting our house trim and/or columns to match? or leave it all white?

also - they are pastel colors but just sample sized gloss from Behr. Not sample sized deck paint officially.

Would the porch flooring then be that same color of charcoal?

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Here is our roof color, currently the front porch isn't shingled. But it's a pretty dark grey/black. Still wondering if that's too dark / strange to match below.

Or I would paint porch and posts

Trevor, if you paint and maintain the siding, it should not need to be replaced. While you own the house. Your goal should be to pass it on as close to original as possible. We repainted our house last summer. Our wood siding was installed over 200 years ago while the metal roof is much younger, installed in 1927. Painting the roof has extended its possible life by a number of years. Paint is protective as well as decorative. We took the opportunity to have the porch ceilings painted a soft, pale blue using BM Glacier Ice ( or Glacial Ice?) in a nod to the glacier that once covered this very property thousands of years ago.

that's awesome - but the last owner put up vinyl siding - which ive heard is iffy to paint anyways? It looks decent enough, but seems to have been installed poorly - since we have had to re-nail certain parts that began to come away.

additionally we're not ready to drop the money to have the whole house painted // we're quite okay with the white

The house is white and you do not want to paint whole house. I am trying to understand what you are wanting to paint. I would not do dark grey on your house,

A few ideas/views;

We at a minimum have to paint the porch flooring

I would paint all the trim white.

I like a medium gray on porch decking. Like this with white on the riser.

I would do haint blue on the ceiling.

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Agree with houssaon. The white trim and white risers with gray porch floor looks clean and inviting to me. Keep your house color the same until you are ready to paint the vinyl siding.

You need to come up with a whole house plan for color. I would find an outdoor rug you really like and pull colors from there. And vinyl takes paint great and it lasts. Since you like the White House color, you could use the colors from the rug for accents.

Denita and Houssaon, the only thing about that is our new steps are stone. While technically the top step is the porch itself. Therefore only the top riser would be white in that scenario.

Here are a few I googled.

I noticed that you had stone steps.

At any rate, I would go with the classic, gray deck paint, haint colored ceiling (I did both my porch ceilings. It is very up-lifting), and all white trim.

You have an American classic! Good luck.