A Glimpse Into a Gatsby-Style Expanse for Opulent Outdoor Entertaining
Want Your Guests to Linger Longer? How This North Shore Estate Sets the Scene for Soirees of All Sizes
When your home overlooks a vast sparkling stretch of Lake Michigan on Chicago’s North Shore, you know you have to share it with family and friends as often as possible.
The challenge for these homeowners, however, is how to carve out memorable moments in a stretch of grassy land previously punctuated only by a swimming pool. The answer lies in thinking of the space as an intimate resort, with vignettes that pull people in with promises of sensory indulgence and a festival of activities—if only for an evening.
The Pull Is Exactly the Point
We spend a great deal of time in this industry talking about how outdoor spaces look and function. The finishes, the furniture, the landscaping. And those things most definitely matter. But the most extraordinary outdoor spaces we've ever designed—and lived alongside—aren't remembered for how they photographed. They're remembered for how they felt to walk toward at 7:30 on a Tuesday evening with 30 of your closest friends joining you.
That kind of magnetism isn't mystical. It has intentional elements. And once you understand those elements, you see them everywhere—and you start to feel their absence in the spaces that don't quite work, no matter how well they're appointed.
We’ll soon be doing the full reveal of a Winnetka home that inspired this ode to outdoor entertaining, but in the meantime, let’s explore the essential elements of an extraordinary exterior space.
The Outdoor Design Elements That Draw You In
Light is the first language
Not the floodlit, evenly illuminated kind that screams parking lot. The kind that pools. That falls in layers—a warm glow at ground level, a candle or lantern at table height, something soft and ambient above. Light that creates zones of shadow as deliberately as it creates zones of brightness, because a backyard with nowhere to disappear into is a backyard that never feels intimate, a backyard with no sweet secrets to keep.
The best outdoor lighting design borrows from what candlelight does naturally: It draws the eye inward and downward. It makes everything within its warmth feel more important and immediate. It puts you at the center of something, rather than underneath it.
This exceptional home uses lighting as an especially enticing invitation: a flickering fire pit serves as a captivating centerpiece, while an upper terrace with U-shaped seating is dotted with umbrellas underlit by chandelier-like illumination.
Softness where you least expect it
Stone and concrete are the foundations. They have to be—this is outdoor living, after all, and it lives in concert with the weather. But the spaces that draw people in inevitably have something soft in the frame: a linen layer that flutters when the wind shifts. An outdoor rug that transforms a hard terrace into something that reads more like a cherished room. Throw pillows in a fabric that shouldn't technically exist outside, and yet somehow is right at home.
Softness signals that someone thought about how this would feel, not just how it would hold up. That signal, whether your guest can name it or not, communicates hospitality. It says: I made this for you to feel welcomed in.
Shade that makes the sun worth having
There's a particular magic to dappled light—the kind that moves across a surface as the afternoon slips into evening, that changes the quality of an hour without anyone adjusting a thing. A pergola covered in climbing plants. A linen canopy that filters without blocking. A mature tree that was planted by someone who loved a property enough to think about what it would become over time.
Here, strategically placed pergolas provide privacy, protection from the sun, and a perfect perch for conversations and gazing out at the water.
Overhead structure doesn't just provide shade. It creates enclosure. And enclosure, in outdoor design, is what transforms an open space into an extension of your home. Without it, a backyard is a yard. With it, it becomes a destination.
Movement as atmosphere
Still spaces can be beautiful. But spaces that live and breathe—that have something in them that shifts and sways and catches the light—feel vital in a way that no static arrangement can replicate. A water feature that adds sound without demanding attention. Ornamental grasses at the edge of a terrace that bend in a summer breeze. Pendant lights on a slinky cord that sway just slightly.
Movement tells the body that time is passing gently. That's the feeling you want at the end of a day. That's the feeling that makes someone look up and realize it's 10pm and they have no intention of heading inside.
Texture underfoot and overhead
The material your bare feet find first thing in the morning. The roughness of a hand-split stone edge. The grain of a reclaimed wood table worn smooth from years of use. Texture slows people down. It makes them notice where they are. And people who are noticing where they are are people who are present—which is, ultimately, the entire point of a beautifully designed outdoor space.
Stay Tuned: Something Big Is Coming
We've been working on an outstanding outdoor project here in the Chicago suburbs that uses every one of these design elements—and a few we're not quite ready to share yet. The renderings alone have made people stop mid-sentence and want to sit with them for a while.
Stay tuned: We'll be showing the full reveal soon.
For now, think about your own outdoor space as summer comes into full bloom. Think about whether it beckons you outside—really draws you, the way a warm room pulls you in on a cold night. Think about whether it has light that makes you want to stay, softness that makes you want to settle in, and furnishings that feel like the indoors have taken up residence under the stars.
If it doesn't, the good news is: Every one of these elements is buildable. Every one of these feelings is achievable. And we know exactly where to start.
Ready to turn your outdoor space into an entertaining oasis? Let’s talk transformation.