I think you’d agree that we don’t get to see enough of the non-perfectly beautiful but super important stuff on the internet that helps inform our design decisions. I had no idea how important having evergreens would be until we lived here through a couple of winters. It’s so gray, wet, and dark in the winter, and if you only have perennials (the showiest flowers, the pretty wildflowers, and generally more my vibe), then the winter looks even sadder. So when Dennis’ 7 Dees reconfigured the sports court and thus added a bunch of landscaping last year, a huge part of the brief was “green, something pretty, year-round”. I was willing to sacrifice and lose some of my favorite varietals for year-round interest. Not like fir trees and boxwood everywhere necessarily, but enough plants that left us with happy visual interest and not just cut-back grasses or lamb’s ears all winter. They agreed, and I trusted them, but it wasn’t until January that I could really see what it would look like, and boy, was I relieved to see that it is indeed so pretty. Now, is it as pretty of a photo tour as summer? Nope. And we didn’t style it at all (or even move our dumb umbrella stands). But I hope it can help you make some decisions, or at least feel seen that you aren’t the only one with a maybe less beautiful yard during the darker months.

Summer 2025:

Our first summer with the recent update was stunning, and we are even more excited about summer #2. There were a lot of things that I never thought I’d love so much (like these incredible hydrangeas). But with so many flowering bushes, what would we see come February?

Here We Are Today, Winter 2026:

Enough green to make me so happy, despite a lot of bare bushes and trees. I know it’s hard to tell with that beautiful southern side light coming in, but when you look out, it still feels full. It should be noted that Dennis’ 7 Dees also maintains our yard, which is not sponsored or discounted, but obviously, having the same company that designed and installed the plants maintain them is a lovely plus. They are super invested in keeping it healthy, and since they know each plant and what the vision is supposed to look like, I barely even need to chat about anything.

Summer 2025:

It’s real park vibes, for sure, in the summer. I’m so excited for this summer.

Winter 2026:

Still really lovely in the winter. Things are obviously not in bloom and cut back, but again, still enough green, texture, depth, and even height variations to delight your eye 🙂

Summer 2025:

Winter 2026:

Shout out to those folding Adirondack chairs that sit out year-round (and were so affordable). I can’t say they are going to last for 10 years because we don’t store them like we should, but leaving them out just looks really inviting (and they are lightweight and fold down, so when we do mow in the winter, which isn’t very often, they are easy to move).

Summer 2025:

The Perrennials around the house really pop off in the summer, but admittedly, by year 4, they are getting pretty dang huge and possibly crowded. I still really love them, though. But winter it’s a different look:

Winter 2026:

So around the house is indeed a lot less full, which should bum me out, but our view is typically from the house looking out, less from the yard looking back. If I could snap my fingers, I’d add some more evergreens around the house (like near the sunroom), but it’s so dang pretty in the summer and we have other areas we want to spend our budget on, so it’s good enough.

Summer 2025:

Winter 2026:

I’m sure if we didn’t have help maintaining it, it would absolutely be messy regardless of the plantings. But I really like how it looks, there is a lot of variation, and enough winter-flowering plants.

Summer 2025:

When we did the area around the pool three years ago, I asked Cali for a plant plan that would show the first summer (because we needed to reveal our Soake pool, so we needed instant prettiness), and I LOVE these wildflowers (I forget what they are called). But we always knew that by year 3/4, they would become super tall and potentially messy (which they were last summer). It looks dreamy in this shot, but compared to the rest of the yard, it feels like a different vibe now. And yet in the winter, they are super cut back.

Winter 2026:

Now this looks totally fine, but in person, it’s mostly just brown. So I am going to pull out some of the unruly tall grasses and put in more manageable plants (ideally some that are evergreen). Honestly, I just want what Eric put in the newer yard, everywhere. Can someone please edit out those umbrella stands? Oh dear. I basically told Kaitlin to go out and take handheld shots to show you the reality of it all.

Here’s where you can really see the difference between the seasons:

One of the flowering winter plants that I’m most pleased with is this one (Laurustinus). We have a lot of Helleborus, which are hard to see in the photos, honestly, but these are still pretty showy (and great for winter flower arrangements). I don’t even remember what they look like in the summer, but I’ll take them for their winter blooms.

Summer VS Winter:

Summer 2025:

Winter 2026:

One of the biggest lessons I’ve learned (of so many) is to forget what you “like” or what you think is “cool” and listen to the experts. I mean, sure, you want the look/feel/vibe/style that represents you and works with the design of your home (ours is casual, wild, natural, colorful, not fussy, not formal, etc), but then lean into what the experts say will THRIVE in your region. Even asking the salespeople at the nursery (if you are in Portland, I seriously am so impressed with Dennis’ 7 Dees). If you have a gardener or landscaper, it doesn’t matter if you jive stylistically; ask them and trust them. I had to learn this the hard way with things like tile installation or even paint, thinking I knew my design and aesthetics and needed to make the decisions. But y’all, they are inherently experts because it’s all. they. do.

Another lesson. Cali (our original landscape designer, who I loved from Studio Campo, who mostly lives in Colorado now) said to us early on that landscape is a living design that evolves a lot. You can’t guarantee how plants will grow or thrive for four seasons. It’s not like furniture in that sense. Even the experts might realize, hmm, this isn’t working a year later and need to tweak. For instance, our lamb’s ear looks great in the summer, but my goodness, it looks like extra garbage in the winter (worse than all our neighbors). So we’ll be making some of those tweaks, too…

Update: New Seating Areas Coming Soon

Remember when I wrote that big love letter to picnic tables? I still love them (and look how good they look in our yard – so simple, natural, and graphic). But last summer, when we had a bunch of school parties with neighbors who didn’t know each other that well, no one sat at them. I think they felt like it was such a commitment to get into, and then you were locked in. People would stand around them and mingle, but no one sat down, and I was so bummed that people weren’t relaxing. So we brought our loveseat and chairs from the back porch down there, and then people plopped down. So this spring I want to move two of the picnic sets along the paddock fence line (for the kids) and create some more casual seating groups for grownups. I’m thinking a firepit area (we used our Solo Stove so many nights last summer) and a lounge set – like two love seats or a small sofa + 2 chairs. Now designing it is proving to be quite the challenge because while I don’t want them all to be matchy, matchy, I really don’t want it to look junky and busy. I also love the wood out here and don’t want a lot of color since the green is the main color, but I don’t want it to be boring either!! Oh, and lastly, yes, I want to be able to leave out at least the frames, ideally not covering them. So getting something high-quality that is really weather-proof is crucial (good luck).

This year, I want to be better about shooting the yard all four seasons – it does change a lot, and Eric, our designer at Dennis’ 7 Dees, did such a great job at selecting plants that thrive year-round. It’s just harder to organize since the weather is unpredictable up here, and only certain times of the day make sense to shoot the yard. I want to make some tweaks near the covered walkway and the kitchen door area (which is our front door basically), so stay tuned on that. But I think they are going to mostly just take what is working back here and plant the same varietals since we know they work and look so good here.

*Photos by Kailtin Green