The Ultimate Guide to Winter Engagement Photos in Chicago
A local Chicago wedding photographer shares thoughtful tips for creating beautiful, cozy, genuinely-you engagement photos during the coldest months of the year.
Hi, I’m Ashley — the photographer behind Artistrie Co., and the one who will happily wander into the cold with you if the light is good (and in winter, it usually is).
I’ve spent 15+ years photographing couples in Chicago, and winter has quietly become one of my favorite seasons: soft light, quieter streets, and a kind of intimacy you don’t get any other time of year.
My approach is candid with an editorial touch — gentle direction when you need it, space to be yourselves when you don’t.
If you’re willing to bundle up, winter can be unexpectedly romantic. I’ll help you see it.
MEET THE PHOTOGRAPHER
Winter in Chicago gets a bad reputation, but for photos? It’s quietly spectacular.
The city slows down. Colors soften. Light becomes this cool, velvety wash that flatters absolutely everything. Even the simplest gestures — holding hands, sharing a laugh, leaning in a little closer — feel more intimate against all that stillness.
Crowds thin out, too. Places that feel packed in summer suddenly feel open and peaceful, almost cinematic. There’s room to breathe, to wander, to settle into the moment without distraction.
And then there’s the light.
Winter sunsets are in a league of their own: pinker, deeper, more dramatic. A kind of magic you can’t manufacture, no matter how good your camera is.
If you’re willing to bundle up, winter gives you something rare — photographs that feel warm in spite of the cold, honest in spite of the elements, and unmistakably yours.
Winter in Chicago gets a bad reputation, but for photos? It’s quietly spectacular.
The city slows down. Colors soften. Light becomes this cool, velvety wash that flatters absolutely everything. Even the simplest gestures — holding hands, sharing a laugh, leaning in a little closer — feel more intimate against all that stillness.
Crowds thin out, too. Places that feel packed in summer suddenly feel open and peaceful, almost cinematic. There’s room to breathe, to wander, to settle into the moment without distraction.
And then there’s the light.
Winter sunsets are in a league of their own: pinker, deeper, more dramatic. A kind of magic you can’t manufacture, no matter how good your camera is.
If you’re willing to bundle up, winter gives you something rare — photographs that feel warm in spite of the cold, honest in spite of the elements, and unmistakably yours.
The Quiet Magic of Winter
One of the best parts of winter sessions — truly — is the wardrobe. Winter gives you permission to layer, play with texture, and lean into outfits that feel beautifully intentional. Think polished coats, soft knits, boots that mean business, a little wool, a little boucle… all the good things.
If you’re taking photos in the cold, dress for the weather, not against it. Let your outerwear be part of the look — the main character, even. A great coat photographs just as beautifully as the outfit underneath, and you’ll be so much happier (and more present) if you’re warm. If the weather behaves or you’re feeling brave, we can always slip the coat off for a few photos. But it’s far better to bring pieces you’ll actually want to be photographed in than something you plan to shed the entire time.
A few things that photograph well and keep you cozy:
– Structured wool coats or tailored puffers
– Boots or closed-toe shoes (your future self will thank you)
– Long dresses, trousers, or tights layered under skirts
– Warm wool socks
– Fleece-lined leggings hidden under anything flowy
– Cozy sweaters with beautiful texture
– Hand warmers in your pockets
– A thermos of something warm (coffee, cocoa, or a little something celebratory)
– Touch-up makeup for rosy noses or windblown moments
– Hats, scarves, earmuffs, gloves — worn in photos or just in between
Winter is a surprisingly chic season, so don’t be afraid to dream bigger with your attire. You can be as relaxed, as elevated, or as glamorous as you want. The key is simple: wear what makes you feel incredible, and what allows you to stay warm enough to actually enjoy the moment.
What to Wear (and Actually Stay Warm)
Winter may not win “Chicago’s Favorite Season,” but it’s secretly one of the most beautiful times to be photographed. There’s a calm to the city this time of year — fewer crowds, fewer wedding parties queued up for their thirty-second in front of a landmark — and suddenly the places that normally buzz with people feel like they belong to you.
The light is its own kind of magic, too. Winter sunsets and sunrises are the best of the year (I will die on this hill). The cold air is clearer, the sun sits lower, and the sky takes on colors that feel almost too vivid to be real. It all translates into photos that look cinematic without even trying.
And if being outside isn’t totally your thing, winter is also the perfect season to get a little creative indoors. Think: a favorite café with steamed-up windows, a museum you love wandering together, a conservatory full of warm air and green plants. These sessions often end up feeling like a very cozy, very romantic date — just with a camera documenting it all in a way that feels natural and quietly intimate.
Perks of a Winter Engagement Session
Let’s name the obvious one: it’s cold. Chicago in the winter has a personality of its own, and she is… unpredictable. If you’re planning a winter session, patience is essential. The payoff — that perfect snowfall, that calm, crisp light — is absolutely worth the wait, but we may need to keep an eye on the forecast and pivot as needed.
Some locations simply aren’t accessible this time of year, whether because they’re closed, icy, or buried under snow. Flexibility becomes part of the creative process — and honestly, winter often leads us to spots we wouldn’t have considered otherwise.
As for the lakefront… can it be done? Yes. Should it be done? Only with caution. The wind off Lake Michigan turns everything into its own Arctic experience — easily 10–20 degrees colder than anywhere inland. Add in potential ice, choppy waves, and slippery walkways, and it becomes a “quick in, quick out, safety-first” situation. When I take clients there in winter, we move fast, stay strategic, and understand our limit (usually about 5–10 minutes before everyone starts to lose feeling in their face).
Winter can be beautiful — truly — but it’s a season that asks you to be prepared, adaptable, and bundled. I’ll guide you through what’s realistic and make sure we’re only choosing locations that feel safe and photograph beautifully.
The Realities of the Cold
If you are planning an engagement photo session in Chicago this winter, here are a few tips for a successful and fun experience!
Winter Engagement Photo Tips
Winter in Chicago is a shape-shifter — soft and dreamy one hour, wildly dramatic the next. That’s part of its charm, but it also means we plan with a little flexibility.
We’ll keep an eye on the forecast together, watching for those days that feel crisp and bright instead of painfully cold. If the wind chill reaches the “why does the air hurt my face?” zone, we pivot. There’s no sense in forcing a vision when you could simply wait for a day you can actually enjoy.
And here’s the secret: the best winter sessions aren’t the ones we push through — they’re the ones we time well. A snowfall, a clear sky, a quiet morning after a storm… winter rewards patience.
When the conditions align, your photos won’t just look beautiful — they’ll feel effortless. Which is exactly the point.
1. Trust the Forecast (and the Flexibility)
Fresh snow is winter’s greatest gift, and also its biggest diva — stunning, but fleeting. Downtown slush appears faster than you can say “salt trucks,” so if snow is part of your dream, we choose locations that hold onto the magic a little longer.
Think Montrose Harbor, Northerly Island, or pockets of the city that feel almost like wilderness after a storm. The kind of places where the snow looks untouched, the air feels still, and your footsteps are the only sound.
And if you’re open to it, planning your session during a snowfall is its own kind of romance. Soft flakes, slow movement, everything a little hushed. Snowfall photographs like a movie scene — cinematic, dreamy, unmistakably winter.
It’s worth timing, chasing, and even rearranging schedules for.
2. If You Want Snow, We Chase It
Winter fashion photographs beautifully — maybe the best of all the seasons. Coats, layers, textures, movement… it’s editorial without even trying.
Think of your outerwear as the main event, not the thing you toss aside between shots. A tailored coat, a textured wool wrap, a scarf with shape, boots you actually like… these pieces create clean lines and intentional styling, even when everything underneath stays bundled.
Choose colors and textures that feel warm and elevated:
soft neutrals,
deep jewel tones,
rich blacks,
cozy knits,
layered textures that add dimension.
Boots and warm socks? Absolutely. Gloves you love? Yes. A hat that feels chic? Go for it.
Warm is not just practical — warm photographs well. When you’re comfortable, you relax. When you relax, you look like yourselves. That’s the whole goal.
3. Dress for the Season (Your Coat Is the Outfit)
Winter is the season that invites you indoors — and those spaces often create the most intimate, editorial-looking photos. Think:
the café you always linger in,
the restaurant where you had your first date,
a beautiful hotel lobby,
a museum gallery you adore.
Indoor moments let you warm up between outdoor scenes, but they also add depth to your gallery — a sense of place, rhythm, contrast, and story.
We can build the session around interiors entirely (a cozy “day-in-the-life” approach), or pair indoors and outdoors for a balanced, cinematic look.
A tiny note of courtesy: some locations appreciate a quick “heads-up” call. Other locations may require a permit or timed entry. Nothing overwhelming — just thoughtful planning so everything feels seamless.
4. Let the Indoors Tell Part of the Story
Winter light is extraordinary — sharp, clean, low in the sky, and far softer than people expect. It wraps instead of glares. It flatters without effort. It adds a quiet intimacy to even the simplest gestures.
Sunrise brings a calm, pastel softness — perfect if you want empty streets and a gentler mood.
Sunset brings the drama: pinks, apricots, violets, rich blues. Some of the best skies I’ve ever photographed have happened in winter, when the sun seems to dip just right and the whole city glows for a few minutes.
Overcast is beautiful too — like a giant softbox. No harsh shadows, no squinting, just pure, even light.
Let winter decide the palette, and the photos will feel unmistakably of the season.
5. Follow the Light (And Let Winter Lead the Way)
Winter has a way of slowing people down — which makes it a perfect season to build a session that feels like a date, not an appointment.
Think cozy, not hurried.
Think intentional, not rushed.
Think “a day that feels like us,” not “posed photos in the cold.”
Share a hot drink, wander somewhere beautiful, duck into a warm space, breathe. Let the cold pull you close, let the quiet create a mood, let the season do what it does best: highlight the small, meaningful moments.
Your photos will look beautiful, yes — but they’ll feel like something, too.
6. Build an Experience, Not Just a Session
If you’re thinking about winter engagement photos — in Chicago or anywhere the Midwest decides to turn quietly beautiful — I’d love to help you dream it up. Whether you’re wondering about timing, outfits, locations, or what this could look like for you, reach out anytime.
You can fill out my contact form or email me directly. Either way, I’m here and happy to help.
Have a question?
Artistrie Co. offers artful wedding and portrait photography in Chicago and wherever your story is unfolding.
