the ART of
ENGAGEMENT SESSIONS
A thoughtful guide to crafting engagement photos that feel like you.
This season of your life is so full and fleeting, and an engagement session is a chance to slow down and notice it. These sessions aren’t just a warm-up for your wedding day (though they do help you feel wonderfully at ease in front of the camera). They’re a small celebration of who you are right now — the sweetness, the comfort, the spark.
Congratulations — truly.
This guide will walk you through ideas and inspiration, but more than anything, I hope it encourages you to choose what feels honest and meaningful to you.
There are no expectations here — just space to be yourselves.
Let’s keep it simple, thoughtful, and beautifully you.
—Ashley
If there’s one thing I want you to know before anything else, it’s this: the best photos come from ease, not effort. You don’t have to perform or prepare or show up with a plan. You just have to arrive as yourselves — a little imperfect, a little busy, a little in love.
Give yourselves a moment before we begin. Take a slow walk, grab a coffee, breathe. Let the day settle. If it’s been hectic (and it usually is), a tiny pause between “real life” and “photo time” makes all the difference. It’s not about getting ready — it’s about softening into each other.
During the session, you don’t need to know what to do. That’s the part I take care of. Your only job is to be present with each other — to laugh, lean in, tease, wander, hold on a beat longer than usual. When you let yourselves enjoy the moment, everything loosens. The photos do, too.
And if you want to turn it into a date, make a little plan afterward — a dinner, a drink, a walk home with no agenda. Something to look forward to, something that marks the moment. That often becomes part of the memory, and somehow, the photos feel richer because of it.
This is meant to feel simple, light, and entirely yours — a tiny celebration of right now.
If there’s one thing I want you to know before anything else, it’s this: the best photos come from ease, not effort. You don’t have to perform or prepare or show up with a plan. You just have to arrive as yourselves — a little imperfect, a little busy, a little in love.
Give yourselves a moment before we begin. Take a slow walk, grab a coffee, breathe. Let the day settle. If it’s been hectic (and it usually is), a tiny pause between “real life” and “photo time” makes all the difference. It’s not about getting ready — it’s about softening into each other.
During the session, you don’t need to know what to do. That’s the part I take care of. Your only job is to be present with each other — to laugh, lean in, tease, wander, hold on a beat longer than usual. When you let yourselves enjoy the moment, everything loosens. The photos do, too.
And if you want to turn it into a date, make a little plan afterward — a dinner, a drink, a walk home with no agenda. Something to look forward to, something that marks the moment. That often becomes part of the memory, and somehow, the photos feel richer because of it.
This is meant to feel simple, light, and entirely yours — a tiny celebration of right now.
The One Part That Matters Most
A few thoughtful notes to help you shape an engagement photo session that feels honest, effortless, and beautifully yours.
How to Build an Engagement Session You’ll Love
Choosing a Place That Means Something
The best locations aren’t always the most famous or the most scenic — they’re the ones that feel like a small reflection of your life together. Places with a little history, a little comfort, or a little spark often photograph the most naturally.
Think about the places you return to without even thinking: your neighborhood streets, the café that knows your order, the spot where you always end up on slow Sunday mornings. These familiar spaces create an ease that shows instantly on camera.
Of course, there’s magic in choosing something a little aspirational too — a museum you love, a beautiful garden, a quiet corner of the city that feels like a secret. Sometimes the right setting pulls you into a feeling you didn’t know you wanted.
And atmosphere matters. Some places feel nostalgic and lived-in; others feel expansive and cinematic. Let yourself gravitate toward the mood that feels most like the two of you.
Once you share what you’re drawn to — cozy, airy, architectural, natural — I’ll help you choose a location that feels honest, effortless, and distinctly yours.
What to Wear
(Made Simple & Beautiful)
Choosing outfits for your engagement session should feel easy and true to you. The best pieces are the ones you slip into and instantly feel relaxed and confident.
Look for fabrics with a little movement or texture — linen, silk, soft cotton, a simple knit, a tailored layer. They photograph beautifully without ever feeling fussy.
Color matters less than how it makes you feel. Neutrals are timeless, pastels are soft, earth tones are grounding, and a bold color can be gorgeous if it feels like you. Think tone and mood, not trends.
For couples, aim for harmony rather than matching. Your outfits don’t need to be the same — just complementary so everything feels cohesive.
If you want variety, consider two looks: one relaxed, one a touch more polished. It gives your gallery balance without overcomplicating things.
And above all: choose comfort. If you’re adjusting or overthinking an outfit, it will pull you out of the moment.
If you’re unsure, send me your options — I’m always happy to help.
Personal photos begin with personal choices. The more your session reflects your real life — your rhythms, your style, your places — the more the images will feel honest and natural.
Start with small things that feel familiar: the café you always return to, the block you love walking, the neighborhood corner that feels like yours. These spaces carry a sense of ease that shows instantly in your photos.
Your connection does the rest. You don’t need big gestures or dramatic poses. Simple things — a hand on a shoulder, a quiet laugh, the way you naturally lean toward each other — often tell the story best.
Think of the session as a little snapshot of your life together right now. If something feels true, it belongs. If it feels forced, we skip it. The most beautiful photos always come from leaning into what feels real.
If you’re unsure how to make things personal, just tell me what you love doing together. We can shape the rest from there.
Personal photos begin with personal choices. The more your session reflects your real life — your rhythms, your style, your places — the more the images will feel honest and natural.
Start with small things that feel familiar: the café you always return to, the block you love walking, the neighborhood corner that feels like yours. These spaces carry a sense of ease that shows instantly in your photos.
Your connection does the rest. You don’t need big gestures or dramatic poses. Simple things — a hand on a shoulder, a quiet laugh, the way you naturally lean toward each other — often tell the story best.
Think of the session as a little snapshot of your life together right now. If something feels true, it belongs. If it feels forced, we skip it. The most beautiful photos always come from leaning into what feels real.
If you’re unsure how to make things personal, just tell me what you love doing together. We can shape the rest from there.
How to make your photos feel personal
And then there are places with their own schedules:
A museum that’s magical right when doors open.
A favorite café that feels warm and intimate before the evening rush.
A garden that glows just before sunset.
If your vision includes a specific spot, we’ll choose a time that lets it shine.
Most importantly — trust that we’ll plan for beautiful light and a relaxed pace. A good session never feels rushed; it feels like you’re exactly where you’re meant to be, together, in the loveliest part of the day.
Light has a way of softening everything — the mood, the colors, even how connected you feel. The most beautiful images often happen when the day slows down a little, and the world gets quieter.
For most couples, that means we aim for early morning or late afternoon into early evening. Not because of a strict “rule,” but because the light feels gentler, more flattering, more true to the moment. Midday sun has its own charm too — bright, bold, and energetic — but it works best in locations with shade, architectural interest, or clean indoor light.
Timing is also about the rhythm of the city.
Weekdays are almost always better than weekends — fewer crowds, fewer wedding parties queued up at the same landmarks, fewer people wandering into the background. If we’re photographing at a popular spot, going earlier in the day or choosing a quieter weekday can make all the difference.
Timing Is Everything
A fresh haircut (ideally a few days before), a clean shave or neatly trimmed beard, and tidy nails go a long way toward a polished, effortless look. The goal is to feel crisp without feeling “done up.”
For the Gents
Try on your outfits a week or two in advance. Make sure everything fits comfortably, moves well, and feels like you. This is the easiest way to avoid a last-minute scramble — and it’s almost always the person who thinks they’re low-maintenance who ends up doing a quick emergency Target run. (I say this lovingly.)
For Both
If you enjoy getting pampered, a fresh manicure or soft, natural makeup can feel lovely for the day. A blowout or simple hair appointment can also take the pressure off styling yourself. None of this is required, of course — it’s more about doing whatever helps you feel relaxed and beautiful.
For the Ladies
A little prep goes a long way
A bit of intentional prep can make your session feel easier — not because you need to look perfect, but because feeling put-together always brings a little confidence with it.
+ Joanna B Artistry
+ Torie Conn
+ Debra Petrielli & Team
+ Erin Graham (hair only)
+ Rare Bird Beauties
+ Goldplaited Salon
These are talented hair and makeup artists I’ve worked with many times and trust completely based here in Chicago. If you’re looking for someone to help you feel polished, comfortable, and beautifully you before your session, they’re wonderful places to start.
My Recommended Hair & Makeup Artists
Want to go a little deeper?
Every time of year in Chicago has its own rhythm — its own light, its own mood, its own kind of magic.
If you found this guide helpful, you might love the deeper, season-specific notes I put together.
Choose your season below and explore what will make it shine.
Guide to Spring Engagement Photos
Guide to Summer Engagement Photos
Guide to Fall Engagement Photos
Guide to Winter Engagement Photos
Seasonal Guides:
Dinner, wine, a walk — anything celebratory. A tiny ritual to close the evening together always feels right.
And afterward? Make it a date.
Parking, traffic, ride-shares — give yourselves enough time so you’re not arriving breathless. Early beats rushed every time.
Transportation: plan it sooner than you think.
If your pup is joining, bring a helper, treats, and whatever usually makes them look at you like you’re the most interesting person alive.
Pets? A delight. Chaos? Optional.
A small bag for keys, phones, wallets (nothing in pockets, I beg of you), plus a lip touch-up, lint roller, a comb, and water. If you’re bringing a second outfit, tuck everything into a garment bag so it arrives unrumpled and unmysteriously wrinkled.
Pack your essentials like you’re going somewhere lovely.
We’ll decide together if conditions require rescheduling — usually the day before. But if you’re the “rain or shine” type, bring a simple umbrella (black, white, or clear — nothing neon). Chicago weather loves drama; we don’t have to join it.
Check the weather
For the ladies: a fresh manicure, a soft blowout or makeup appointment, or simply a little extra time with your favorite products.
For the gents: a clean shave or tidy beard, a haircut a few days prior, and trimmed nails (yes, really — hands are in photos).
For everyone: avoid last-minute experiments. Familiar is best.
A quick grooming refresh never hurts.
Not in a dramatic, fashion-show way — just enough to make sure zippers zip and hems hem and no one is discovering a missing button fifteen minutes before we begin. Steaming or ironing things the night before is one of those unglamorous little acts of kindness your future selves will appreciate.
Try Everything On
A day or two before your session, give yourselves a little space to get ready. Not “wedding-day” ready — more like “the version of you that feels calm, put-together, and not frantically searching for an iron at 4:27pm.” A little preparation goes a long way.
