The ultimate guide to fall engagement photos in chicago
Thoughtful tips for creating warm, stylish, beautifully personal fall engagement photos in the city.
Hi, I’m Ashley — the photographer behind Artistrie Co., and someone who pays close attention to the way Chicago changes in the fall. The warm light, the golden trees, the quiet calm that makes everything feel a little more cinematic.
I’ve spent over 15 years photographing couples here, learning how each season shapes a story. Fall is where my work — candid, romantic, quietly editorial — feels most at home.
My approach is simple: gentle direction when it helps, space to be yourselves when it matters. Nothing forced, nothing fussy — just honest, beautiful moments.
If autumn feels like your season, I’d love to show you how stunning it can be.
MEET THE PHOTOGRAPHER
Chicago in the fall is a different city. The edges soften, the colors turn dramatic, and suddenly the whole place feels like a very stylish film set. Honestly, it’s hard to take a bad photo.
There’s a calmness to it — fewer crowds, gentler light, more places to tuck into without dodging tourists or bikers or an entire family reunion. You can actually take your time.
And the foliage? Not subtle. In the best way.
Gold, copper, deep berry reds — all those warm tones make everything (and everyone) look incredible. Add a little movement, a cozy layer or two, and you’re basically done.
Fall is one of those rare seasons that does half the work for you. You just show up, lean in, and let the city do its thing.
Chicago in the fall is a different city. The edges soften, the colors turn dramatic, and suddenly the whole place feels like a very stylish film set. Honestly, it’s hard to take a bad photo.
There’s a calmness to it — fewer crowds, gentler light, more places to tuck into without dodging tourists or bikers or an entire family reunion. You can actually take your time.
And the foliage? Not subtle. In the best way.
Gold, copper, deep berry reds — all those warm tones make everything (and everyone) look incredible. Add a little movement, a cozy layer or two, and you’re basically done.
Fall is one of those rare seasons that does half the work for you. You just show up, lean in, and let the city do its thing.
Why Fall Works So Well
Fall is the season for texture, warmth, and really good color — which makes it one of my favorites for engagement photos. Think less “Pinterest palette” and more quiet, romantic September light meets your actual lives.
Start with pieces that feel good the moment you put them on. Soft knits, tailored coats, silk skirts, a beautiful sweater with sleeves that fall just right — fall is generous when it comes to textures that photograph well.
Color-wise, lean into the mood of the season. Deep greens, warm browns, wine, rust, charcoal, cream. They play beautifully with Chicago’s changing trees and that dreamy, golden fall sun. Bright pinks and electric yellows can fight the landscape a bit, but richer tones feel effortless, even cinematic.
Layers are your best friend — not just for warmth, but for shape and movement. A structured jacket, a scarf with texture, a long coat that catches the breeze… everything becomes part of the story.
And truly: comfort matters. If you’re tugging, adjusting, or overthinking your outfit, it will pull you out of the moment. Choose pieces that let you walk, sit, cuddle, spin, breathe.
If you’re debating between options, send them my way — helping you style your session is one of my favorite parts.
What to Wear for Fall Engagement Photos
Fall in Chicago has this way of making everything feel a little more cinematic. The light softens, the colors deepen, and suddenly the city feels warmer — even when the temperature drops.
Trees turn every shade of gold and rust, framing the skyline in a way no other season can. Lincoln Park feels almost storybook, the Riverwalk glows at sunset, and even the hum of downtown takes on a calm, honey-toned softness. It’s the kind of atmosphere that makes you lean into one another without really trying.
The weather helps, too — cool enough for layers (which always photograph beautifully), but still comfortable enough to wander, explore, and settle into the moment. You can walk from a tree-lined path to a skyline overlook without breaking a sweat or losing that cozy, wrapped-up fall feeling.
And maybe the best part? Fall seems to bring out something honest in people. You’re not performing for the camera; you’re just existing in a season that already feels nostalgic and romantic. The photos reflect that — warm, grounded, intimate.
If there’s a time of year Chicago feels like a love letter, it’s fall. I’d love to help you capture it.
Why Fall Just Works
Fall in Chicago is gorgeous — but she’s also dramatic. One day it’s crisp and golden, the next it’s moody and misty, and sometimes both within an hour. It’s part of the charm, but it does mean we plan with a little flexibility.
Crowds are another truth of the season. When the leaves peak, everyone comes out — runners, families, tourists, a half-dozen photographers all waiting for the same patch of trees. Nothing we can’t work around, but it helps to go in knowing fall is... popular.
And then there’s the daylight. Shorter evenings mean sunsets arrive quickly — beautiful, but fleeting. Timing becomes important, which is why I help map out the session so we’re using the light intentionally, not racing against it.
None of these things are dealbreakers. In fact, with a bit of planning, they barely register. We choose smart locations, avoid peak times, build in extra breathing room, and let the season do what it does best: create magic.
Fall always gives more than it takes — we just treat her with a little respect.
A Few Realities of Fall (So You’re Not Surprised)
If you’re planning a fall engagement session in Chicago, here are a few things that make the experience smoother, lovelier, and a lot more fun.
Fall Engagement Photo Tips
Fall does so much of the work for you — the color, the texture, the mood. Lean into it. Think tones that feel like they belong in the scene: moss, wine, camel, cream, tobacco, charcoal, rust. Nothing has to match perfectly (in fact, please don’t), but when your outfits echo the season instead of fighting it, everything looks instantly elevated.
Texture is your friend here: wool, silk, soft knits, a structured coat, a scarf with a little movement. All of it photographs beautifully and gives your images that editorial, effortless quality — the kind that looks intentional without trying too hard.
1. Let the Season Do the Styling
Chicago’s fall light is exceptionally flattering — softer, lower, more golden than summer ever bothers to be. If you can swing it, choose early morning or late afternoon. This is when the trees practically light themselves and your skin tone gets that warm, cinematic wash that no amount of editing can fake.
In the height of fall, golden hour really earns its name. Everything gets a little glowy around the edges. It’s worth planning for (or waking up for, if you’re morning people).
2. Time It for the Glow
Fall thrives in places with depth — tree-lined streets, paths where the leaves pile up, quiet corners of Lincoln Park where everything turns gold at once. Even simple spots, like residential blocks or the stretch of trail you walk on Sundays, can photograph beautifully when the color hits.
If you’re up for a short drive, the Morton Arboretum feels like autumn dialed up to eleven. But honestly? Some of the best fall photos happen in the spots you wouldn’t expect: a tiny pocket park, a quiet side street, a neighborhood with mature trees and very little foot traffic. I’m always happy to help find them.
3. Choose Locations with Layers
Fall has this built-in sense of motion — crisp air, leaves underfoot, jackets that catch the breeze. Let’s use that. Walk, link arms, adjust a scarf, pull each other close for warmth. The more you move, the more natural everything feels.
This is where the magic usually happens: the in-between moments, the half-laughs, the quick glances you don’t overthink. Movement gives you permission to relax a little, and the photos always reflect that.
4. Invite Movement
A little comfort goes a long way. Hand warmers in your pockets, a thermos of something warm (coffee, cider, wine if you’re feeling bold), a soft blanket for between shots. You won’t need them constantly, but they help keep the mood light and the energy from dipping.
Think of it less as “surviving the cold” and more as setting yourselves up for an hour of feeling good and being present. When you’re warm, you’re relaxed; when you’re relaxed, the photos feel like you.
5. Keep the Vibe Warm
Fall is famously unpredictable — bright sun one minute, clouds rolling in the next. Instead of fighting it, we’ll work with whatever the day gives us. Overcast light is actually incredibly flattering; rain can be romantic in a very “October movie” way; and a moody sky adds drama you simply don’t get in other seasons.
We’ll keep an eye on the forecast and pivot if needed. But flexibility tends to pay off — some of the best fall portraits happen on the days that didn’t look perfect on paper.
6. Let the Weather Be Part of the Story
Not a “prop,” not a theme — just something small from your real life that softens the photos and makes them feel lived-in. Maybe a shared coffee from your favorite shop, a dog who insists on being included, a book you both love, a blanket from your home, a place you gravitate toward every weekend.
These aren’t staged moments; they’re little pieces of your life that make the session feel personal. When you add even one, the photos shift from “pretty fall pictures” to “this is us right now.”
7. Bring One Thing That Feels Like You
If you’re dreaming up fall engagement photos in Chicago and want to chat through ideas, reach out anytime. You can email me directly or send a note through my contact form — I’d love to hear what you’re thinking.
Have a question?
Artistrie Co. is a wedding & portrait photography boutique serving Chicago and beyond.
