Painting Old Cedar Shingle Siding

My Painted House Part II

Last time on My Crappy House, we primed the front to get ready for painting the old cedar shingle siding. I don’t know about you, but when I’m working on a project on my crappy house and looking for inspiration, I tend to notice everyone else’s crappy houses. OK, most of them aren’t so crappy, but some of them totally are…

Ugly multi-colored house
(Note to self: Garden Dinosaur)

This is especially true when I’m working on my crappy house’s exterior, because it’s easy to look at the outside of people’s homes without permission. The streets are public (mostly) and you can check them out while (slowly, but not too slowly) driving by.


You can park your car down the street, get out with your paint swatch book, sneak up to a house, color match the siding, then run away! As long as no one sees you, it’s totally OK!

(Don’t quote me on that.)

Woman hiding behind fan of paint swatches

Choosing a Paint Color

Making decisions is not one of my best skills. You guys know…

About twenty different peacock blue swatches painted onto a wall

But planning fictitious covert ops, strangely, is one of my best skills. Who knew?

ARVE Error: Mode: lazyload not available (ARVE Pro not active?), switching to normal mode

Operation “Sneak up to a stranger’s house to match their siding color without anyone noticing and calling the cops” was a success!

Woman in trench coat holding swatch book winking at camera giving thumbs up

So, what do you think I picked? Let’s do a Pointless Poll!

Well, that was fun! AND informative!

Painting the Old Cedar Shingle Siding

When you last saw my crappy house, it looked like this:

House with cedar shingles primed in a light gray

All primed and ready for paint! (If you missed that post, it’s here in part I.) It looks quite nice, I think, in the light gray. But I prefer a little drama, so we went a bit darker…

Gray square matching Kendall Charcoal Paint by Benjamin Moore

That’s “Kendall Charcoal” from Benjamin Moore. Guys, I picked a color from the book! This was not a custom color! Who am I?

This color is darker than the vinyl siding we put on a year or so ago. If I had known I would want to go this dark on the front, I may have picked a darker vinyl, but I kind of like the colors being different. They compliment each other and I get to have the “drama” in the front with a more “relaxed” gray in the back. It’s like a house color mullet, if you will.

Piece of gray vinyl siding with a gray paint swatch on top to match

It’s the bottom swatch. Yep, it’s dark. Don’t be scared. It’s not your house.

I had the color mixed at Sherwin Williams because they have good quality paint, AND they run a sale twice a year for 40% off. The color matches the Ben Moore swatch perfectly and I really enjoy saving money.

Open paint can showing gray Kendall Charcoal paint

I may have mentioned in the Part I post, but in case I didn’t, I want to be very clear that painting shingles sucks. It sucks so bad. If being happy is important to you, then you should avoid painting shingles. And if you have to paint shingles, I would suggest using a paint sprayer and not brushing it on like we did. Apparently, we enjoy misery.

Cedar shingles with dark gray paint cutting in around edges
Garage with dark gray paint cut in around cedar shingles

I did most of the crevices and cutting in while Schmoopy painted the faces.

Man on precariously placed ladder painting cedar shingles gray on garage

I told him that’s not how you’re supposed to do the laddering…

Front of house with left half painted gray and right half primed light gray
Progress of painting cedar shingles dark gray

We did two coats of paint over two coats of primer. How cool is it that this

White ranch house in run down condition

now looks like this?

Ranch house with cedar shingles painted dark gray

Isn’t it amazing what a bit of paint and a lot of work (like, seriously, a lot) can do?

(And also a new bay window and trim.)

Now I just need a garden dinosaur. And a garden. And a driveway. And a fence. And a pony. 

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  • Julia Curtis

    I love your very randomly timed posts. Just when I forget all about you…hey! you’re baaaacckkk! You really need to YouTube a tour of the crappy house, because I’m a very visual person and even though you don’t know me I am important. Love the progress. You’re welcome.

    • My Crappy House

      Right? I’m like a bad penny, but in a good way! I absolutely do plan to do a video tour at some point, but it has to coincide with the rare occasion when my whole house is clean. With photos, I can push all of my crap outside the picture, so no one knows what a slob I am. I do appreciate your importance though, so I will work on that ASAP.


    Gorgeous! I’m happy for you but concerned for us as it seems you are nearing the end of your project. What are we to do when your house is no longer crappy? You can’t abandon us. What will you do next?

    • My Crappy House

      Not to worry! I will always have crappy stuff to talk to you about. I still have the master bedroom that I haven’t done a thing with, the basement that we want to finish, other random inside projects and lots of outside projects, not to mention Egor and Zero. You’re stuck with me for a while…

  • Julia

    Holy Crappy Day!!! We get a post AND a video??? Forget Groundhogs and Super Bowls! It’s My Crappy House Day!! And it’s looking less crappy. Keep it up!

  • judy

    I like it,very somber-for a gal with personality and Pizazz to spare! Can you come up with a garage door and window trim paint that states (ALL CAPS) A really interesting human resides here….!!!! Black? Diagonals on Garage of? Weird? Wadda eye know..nuttin. Love your posts,always make me smile.

  • LaFawne

    Our house is med dark gray trimmed in white so of course I love yours! Also, in years past, I have actually stopped and knocked on the door of a house to ask what color they used. My husband waits in the car and tries to look like he doesnt know me

    • My Crappy House

      Aww, you’re right! I’m so sorry. BUT, I’m working on a post that’s all about Egor. Hopefully, that will make up for the lack of kitty in this post.

    • My Crappy House

      Haha my Pantone book is really old, but if 227 is still the same as it was 10 years ago, Ima have to emphatically veto that color!

  • Katherine Davies

    Oh my gosh! So long since we’ve heard from you! Not a problem, just mentioning it. ? Unfortunately, my iPad will not allow me to see your photos. Boo. The video was cute, though. Your hair is really long and pretty! Wish I could see the very-not-crappy color on your crappy house,

    • My Crappy House

      Hey, when you’re right you’re right. But three months isn’t the longest you’ve gone without a post from me, so maybe I’m getting better? I dunno. We can hope. Anyway, the same laziness that keeps me from posting also keeps me from getting haircuts, so it just keeps on growing! Thank you for the compliment though

  • Carole

    Love the POP! of the dark grey; and the lighter grey in back! Smart choice. I’m still laughing at the video? because that is exactly what I’ve been contemplating in my neighborhood. I’ve got a yellow ( love it!) house now sitting on (harvest stone) foundation. Have to paint either cream or darker eggplant. Also love the leveling of ladder; must remember that ?

    • My Crappy House

      I’m glad you liked the video. It’s fun to be silly! If you remember anything about that ladder set up, please remember to not do that! He’s lucky to be alive…

  • Cecile Lowrey

    I live with my sister In a pretty crappy house too because that is how it is painted…two colors of crap colored paint. With a million untrimmed shrubs and trees. We are 70 year old twins with little money or strength left so it probably won’t change. I like the work you have done on your house.

    • My Crappy House

      Aww, I’m sorry you have to accept your crappy house the way it’s painted. Any chance it actually looks charming? Anyway, as long as you have heat, hot water, and a roof that doesn’t leak, you’re doing OK

  • Le

    Amazing progress on the house!
    Schmoopy is a daredevil. I hope you have workers comp or insurance. OSHA might shut you down for that ladder work.
    Also, Egor gets a whole post to himself? What about Zero? Always an over looked step child… >.<

    • My Crappy House

      Of course Zero is in the post, but they didn’t ask about Zero. They only asked about Egor. We love Zero…

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