Advice from a Professional House Painter (+ Selecting a Paint Color for the Two Flat!)

This post is sponsored by Lowe’s Home Improvement. Painting the exterior of a home is a large undertaking that requires a lot of consideration, so today we’re interviewing Jim Amatore, owner of Chicago Painters Inc., to help us take the mystery out of the process.

Paint sample chips in various shades of medium to dark green are laid out on vintage pine flooring // via Yellow Brick Home

Narrowing it Down

Selecting a completely new paint color for the Two Flat is incredibly exciting, but also incredibly scary! After all of the time and effort we put into the revised exterior of the home, the final color palette is something we need to get right the first time. We’ll be giving our Two Flat a massive exterior makeover with the help of Lowe’s, where we’ll be sourcing all of our supplies. Think: exterior paint for the siding and trim, stain for the front porch and back deck, and landscaping for the yard! We’ve been daydreaming of this day, and we can’t believe this transformation is finally happening.

In addition to hunting for the perfect colors for the home, we were also on the hunt for the right company to hire for the job of painting her. After a few great meetings and conversations, we went with our gut and hired Chicago Painters Inc. They’ve been in business for almost 20 years, and the owner of the company, Jim Amatore, offered to share some of his knowledge about what to look for in an exterior painting company. Let’s start from the beginning and talk about the hiring process:

What are some important considerations to take before hiring an exterior painting company? 

“Online reviews are crucial. Be sure to double check the company you want to hire on Yelp or a similar site, and have them send you a copy of their insurance listing you as an ‘additional insured’ for protection. You’ll also want to make sure they have workers compensation. Some painters might skip this insurance because it can be expensive, but it’s one possible reason why one company may be 20-30% different in price from another.”

The front of our Two Flat with paint swatches // via Yellow Brick Home

Throughout the color selection process, Jim let us know that they even have an interior designer on staff that is available for custom color consultations. If you’re not sure where to start with color, we urge you to pull inspiration from online, print and, of course, in-person! Surely you’ve seen homes you love when strolling the neighborhood, right?

We already had a strong vision of how we wanted the house to look, so we didn’t take advantage of the optional color consult service ourselves, but it’s so great to know that similar resources exist!

Making the Right Choice

As a rule of thumb, we always grab way more samples than we think we need because it can be tough to predict how each color will read in a space. For this step, the more the merrier! As the front of the house came together, we couldn’t shake the idea of a deep green that would play nicely with the brick buildings on either side of the home, but were cautious of going too dark, (even though dark, black-green shades are on-trend at the moment).

Various shades of green paint sample chips are taped to the exterior siding of a house // via Yellow Brick Home

Once we had eliminated the colors that weren’t quite right, the final contenders were Valspar’s Cosmopolitan Olive, Sherwin Williams Shade Grown and Sherwin Williams Woodland Lichen. We used paint samples from Lowe’s to paint larger swatches on the house in various areas, so that we could see how these colors react in different lighting situations.

Three varying shades of olive green paint samples as they're applied with sponge brushes // via Yellow Brick Home

Much like with paint colors, we’ve grown to trust our gut with contractors, but made sure to ask Jim if we were on the right track with our usual quote-gathering process.

How many quotes would you suggest gathering, and how should the homeowner make their final decision? 

“Sometimes one quote is enough! If you like the painter and they have good online reviews, great! If you’re on a strict budget and need the best price, then get 3 estimates. If you find a contractor that you’d really like to work with but they’re beyond budget, you can always ask them if there are slower times of year where they offer discount opportunities.”

This is great advice and something we’ve implemented in the past as well. We’re also big fans of asking contractors if they can offer a price break for cash/check payment to avoid credit card fees. Jim agreed that this is good practice, as long as both parties benefit from negotiations.

Three shades of olive green paint samples as they're applied with sponge brushes // via Yellow Brick Home

Avoiding the Wrong Choice

As with choosing the paint color for the home, choosing the right contractor to apply the paint is crucial as the wrong decision can have long-term consequences. With this in mind, we asked Jim:

What red flags should a homeowner look out for when hiring a painting contractor? 

“How fast do they call you back? If a company hasn’t called you back in 48 hours, they are likely too busy and might be implying that by not responding right away. If you have to call a painter 2 or 3 times to get them to send you the proposal they promised to send you, they may not be the right fit for your job at all. Don’t feel offended or feel the need to stay on top of them to get you the promised proposal. Just move on to the next painter until you find one that is interested and eager for your business!”

This is fantastic advice! If it’s difficult to get a hold of a contractor before the work starts, how difficult will it be if there’s an issue once the work is complete? We’ve definitely been in a situation where we can’t get a single person to call us back, and this is a blunt (haha) reminder that there’s a reason why that happens.

Olive green paint samples are applied to new siding with sponge brushes // via Yellow Brick Home

Preparing for Painting Day

Once the final color has been selected and the painting contractor has been hired, it’s time for everyone to prep for the work to begin! This final step should include a conversation to clarify a few things. For example, who is purchasing the paint? Whose responsibility is it to move patio furniture or anything else that might slow down the painting crew? Will the crew need access to the neighboring yards?

Here in Chicago, our homes are generally very close together and sometimes access to neighbors’ yards is necessary, so it’s good practice to get permission ahead of time. Every painting crew will likely have different answers to my prep questions above, but we asked Jim what we could expect once the painting commences!

What should the homeowner expect on the first day of the paint project?

“The basic prep should include cleaning, sanding and covering. If a painter walks in and starts painting, you’ll have problems down the road!”

As we always say, applying the paint or stain is a fairly small portion of the overall project. The prep work should be very thorough. A lack of proper preparation can lead to premature paint failure and added expense down the road, so it’s important to be as thorough as possible on this crucial step!

Three different olive green paint samples have been applied to new siding on a house under construction // via Yellow Brick Home

The Final Choice?

We’re very excited to be working with Jim and the team at Chicago Painters Inc (if you’re in Chicago, you can get a free estimate right here), but what’s the final color choice? We’re waiting for a string of nice weather days to get started on the project, so the big reveal will have to wait! (Aka, we. are. still. torn! What do you think?)

A Chicago house under construction sits between two vintage brick buildings // via Yellow Brick Home.

In the meantime, we’re gathering up the paint tallies we’ll need to paint and stain the Two Flat, and then we’ll be placing our big online order through!

As friendly reminder, Lowe’s is offering free curbside pickup through these unique and challenging times. Thank you, as always, to our friends at Lowe’s for supporting our renovation journey.

PS: You can see what the exterior of our house looked like on closing day right here. What a world of difference already!

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  • Susan4.30.20 - 7:33 AM

    Not that there are any hard and fast rules, but I’ve generally heard a house should have a minimum of 3 colors for depth and interest and to highlight the details. So decks are one color, door is another, trim is the third and for this house maybe the triangle just below the roof is the 4th color. I would want to know your trim color considerations before voting on which green to use for the body. Shade green looks too dark on my little phone. I would worry the house could easily go towards gloomy with that color. The yellow green could be fun with cream and terra cotta accents that would be a nod to the surrounding brick buildings while still standing out. But that doesnt seem like a color trio you would choose. It’s going to be so fun to see where you land on this! Cant wait!ReplyCancel

    • Kim4.30.20 - 9:06 AM

      This is such a good point to bring up! We’re also testing stain colors this week, and we’re narrowing in on our final choices. White trim and railings, green body and a warm gray for the treads. We’ve also chosen a warm transparent stain for the tongue and groove porch ceiling!ReplyCancel

  • Karen T.4.30.20 - 7:53 AM

    My eye was immediately drawn to SW Woodlawn Lichen but it definitely has a blue undertone. Leaning towards SW Shade Grown but they are all pretty. Cannot wait for the final reveal!ReplyCancel

    • Kim4.30.20 - 9:03 AM

      Woodland is sooooo pretty, but you’re right, there was too much blue in it for what we had in mind.ReplyCancel

  • Dc4.30.20 - 8:39 AM

    They are all very pretty. If I had to choose, probably the lichen and then the olive. Shade grown is pretty….but we painted our house a dark green and it showed fade quickly. Green can be tricky that way. ReplyCancel

    • Kim4.30.20 - 9:03 AM

      That’s what we’re concerned about, but I also thought… since Olive is a step lighter than Shade Grown, maybe it’s better to go darker now, knowing that it will fade?ReplyCancel

      • Betsy4.30.20 - 12:05 PM

        If the house is prepped properly, fading shouldn’t be too big of an issue.  But it also depends upon the type of siding being painted.    The Sheen, or lack there of, can also result in fading.  My neighbors painted their shingle sided home a color similar to Shade Grown.  Has not faded in the 5+ years since it was painted. I have the same shingle siding, and have a deep charcoal on my house.  I got a crappy paint job, even though they were the most expensive.  My house color has faded, and already peeling after just 2 years.  Team Shade Grown for the win.  Cosmopolitan Olive comes in second place.ReplyCancel

        • Kim4.30.20 - 1:52 PM

          Oh, how interesting! What part of the prep process do you think caused your paint to not hold up as well? We’re learning a lot from our contractor, and hoping he’ll be back to share some prep + process tips once we get going.ReplyCancel

  • Dave4.30.20 - 8:44 AM

    We vote for shade green! Thanks for turning us on to Sherwin Williams and Valspar paints from Lowes. They are by far superior to any paints we have used in the past.ReplyCancel

  • Deb4.30.20 - 8:45 AM

    Shade Grown!ReplyCancel

  • Danielle4.30.20 - 8:50 AM

    It’s a tough choice, but I vote for Shade Grown! Since there is both red and yellow brick on the neighboring buildings, I think the more neutral undertones of Shade Grown would look the best. ReplyCancel

  • Leslie4.30.20 - 8:50 AM

    Shade Grown.ReplyCancel

  • meredith4.30.20 - 8:57 AM

    I’m torn too – I think my first choice would be cosmopolitan olive and then shade grown. We had our house painted a few years ago and I completely understand the hesitation, especially on such a big project. I’m not 100% happy with our final color, although it’s grown on me, and took me a while to like it more than I initially did. There was something about the change that just threw me off. It was a good learning experience because I have a much better sense of what I’m looking for in our next house. :)ReplyCancel

    • Kim4.30.20 - 9:01 AM

      Now I need to know what color you painted your house!ReplyCancel

      • meredith5.1.20 - 9:34 AM

        I chose sherwin williams acier – and I definitely walked around our neighborhood with the swatch and sneakily compared it to a house that I liked, lol. I wish it were a bit richer and I don’t love it next to our neighbors house, although they have creamy beige-yellow siding so I wasn’t going to plan around that. On a separate note, would love to see a  big-picture post about the two flat that lays out what’s left to be “done” and shares information about timing, road blocks, thoughts, etc. Cheering you all on through this process!ReplyCancel

        • Kim5.1.20 - 10:46 AM

          That’s a great idea, thanks, Meredith! ????ReplyCancel

  • Molly4.30.20 - 9:00 AM

    I love the woodland lichen and shade grown swatches!  Have you tried the other sides of the house, too? ReplyCancel

    • Kim4.30.20 - 10:29 AM

      We’ve held up the swatches, but technically our home only has 2 sides we can see – the front and back! The back is almost always shady (and faces an alley), so we really want to make sure we get the front right.ReplyCancel

  • Brenda4.30.20 - 10:31 AM

    Olive seems too yellow and Lichen seems too blue, but I love SW Shade Grown. ReplyCancel

  • Elizabeth4.30.20 - 10:45 AM

    The lichen shade is definitely my favorite, although I expect you’ll end up on the olive color. I have no doubt it will turn out gorgeous whatever you choose!ReplyCancel

  • Lorraine4.30.20 - 11:29 AM

    We painted our house a few years back and on the gallon of paint I noticed a small note *not recommended for exteriors. Ack. Too late. This year we took out a bush in the front and can very clearly see how much the paint had faded over timeReplyCancel

    • Kim4.30.20 - 11:46 AM

      Oh no! Do you remember what paint you used so we can warn others?!ReplyCancel

  • Viktorija4.30.20 - 1:07 PM

    I love Shade Grown! :)ReplyCancel

  • Kirsten F4.30.20 - 1:31 PM

    Cosmopolitan Olive! It’s fresh & original and would look awesome in between the two next-door buildings!ReplyCancel

  • Caitlin4.30.20 - 1:42 PM

    I’m loving the olive color here! 
    I painted my house a dark green last summer. I too tested a number of color swatches around the house to decide on my color (SW pewter green) but it ended up looking darker than I had originally imagined. I was also going from a lighter tan color to a dark green, I definitely think the surface area of the color impacts the overall tone. Luckily I love how my (darker than expected) house turned out. Can’t wait to see yours once it is painted! ReplyCancel

  • Monique4.30.20 - 2:52 PM

    Three great options! Personally, I was immediately drawn to shade grown.  Olive feels too military green (which I’ve had enough of in the military haha). Lichen has a beautiful teal undertone, but it doesn’t seem as dark as you want to go (I think, if I remember from your stories). Shade grown doesn’t look too black/green from the top swatch. Are you able to paint swatches closer to the wooden porch ceiling?  I think it might make your decision a little easier (and the deeper green of shade grown might look really good with the golden wood) ???? good luck!ReplyCancel

  • Kira4.30.20 - 3:36 PM

    First of all, I feel you on this one, because I am about to have the exterior of my house painted for the first time next week, and deciding on exterior paint colors is one huge, anxiety-inducing decision! I love a moody paint color, but I think Shade may read too dark in between your lighter neighboring houses; and Woodland may be too blue, so I’d go with Olive! So so pretty, and I think it will also look great with *any* stain color you choose. Can’t wait to see the final reveal!ReplyCancel

  • El4.30.20 - 3:50 PM

    Seems like you have 3 good colors so maybe that is why it is so hard. I’m partial to the SW Shade Grown though.
    I’m curious how do they handle the painting in that narrow space between the houses? Seems like an accident waiting to happen for me at least to get paint on the other house. I’m sure they are used to it and there are tricks so I’m curious.ReplyCancel

    • Kim4.30.20 - 5:44 PM

      They’re going to go as far as they can!ReplyCancel

  • Kaitlin4.30.20 - 5:41 PM

    Shade Grown is my choice, but we all know you guys will knock it out of the park with whatever you choose!ReplyCancel

  • Susan4.30.20 - 7:12 PM

    Is the very top triangle wood or some type of non-wood siding?   My sister was thinking of painting her non-wood siding a darker color, and was warned that the pant can absorb heat and distort/melt the siding.   There are specially designed paints that dissipate the heat (through the magic of science, I guess) and allow siding to be painted dark colors safely.  Just an FYI.ReplyCancel

    • Kim4.30.20 - 8:29 PM

      I haven’t heard of that, but it makes sense! The exterior paint we’re choosing is formulated for our siding, so we should be al good. We have LP Smartside on the front, and it’s aluminum on the white peak, sides and back.ReplyCancel

  • HeatherB5.1.20 - 6:57 AM

    I like shade grown.  Seems dark, but on large exterior spaces will probably be fine.   Olive seems a little too brown and lichen a little too blue, imho.  Any of them will likely be fine.  And I’m looking forward to seeing how it makes the two flat pop next to the neighboring buildings!ReplyCancel

  • Bobbie5.1.20 - 9:15 AM

    This looks like a really cloudy day from the photos and maybe this isn’t an issue where you live but the sun will add a VERY distinct yellow to whatever color you choose so keep that in mind. That was the best advice we got from our free color consult with from our painting professionals since we live in a very sunny location.ReplyCancel

    • Kim5.1.20 - 10:45 AM

      Yes, absolutely! And the front of the house gets southern exposure all day long.ReplyCancel

  • Mandy5.1.20 - 10:49 AM

    Another vote for Shade Grown :)ReplyCancel

  • Barbara Flynn5.2.20 - 8:26 AM

    So excited to see the final choices and results.  I kinda like cosmopolitan oliveReplyCancel

  • Shelly5.3.20 - 1:26 PM

    What type of sheen do you go with for an exterior? ReplyCancel

    • Kim5.4.20 - 9:39 AM

      Our painter recommended a low lustre sheen for the body, and satin or semi-gloss for all the trim. So we’re using flat for the main part and satin for all the trim!ReplyCancel

  • at home with ashley5.4.20 - 1:14 PM

    Shade Grown is gorgeous! It’s a little more formal than the other two colors and has good depth.ReplyCancel

  • Ann5.8.20 - 2:29 PM

    We used SW exterior paint with a sheen about 6 or 7 years ago. It has held up admirably! My house is tan; neighbor has deep green (also SW) which has held up w/o fading or peeling.ReplyCancel

  • Kay5.28.20 - 6:54 PM

    I love Shade Grown, although my second choice would be the olive. Woodland Lichen seems just a little too blue. I don’t think you can go wrong with any of these colors though depending on what color you decide to go with for the porch stain. 

    Can’t wait to see the final exterior reveal!ReplyCancel

  • painting contractor3.11.21 - 10:14 PM

    Thank you for sharing your wonderful journey. I love the outcome. The renovation is really stressful and it is nice to know you have a lot of help for this one. I am looking forward to more renovation stories from you. Cheers!ReplyCancel

  • Sheila Boserio3.29.21 - 11:05 AM

    House painting is one of the most important home maintenance projects you can do. House painting upkeep and caulking help protect your home from weather damage caused by water and sun. Neglecting obviously peeling exterior paint can lead to high siding replacement costs. Thank you for sharing your wonderful experiences as a skilled painter. Best regards from our <a href=”“>commercial painting contractors</a> in Virginia.ReplyCancel

  • Ella Starr5.12.21 - 1:44 PM

    How great that you talk about how choosing an exterior paint color and wanting to get it right the first time. I just purchased my dream home and I want to paint it yellow. I will look for a reputable exterior painting company in my area.ReplyCancel


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