How to Get Picture-Perfect Holiday Photos Without the Stress

You know the scene: you’re wrangling kids into coordinated outfits (that they suddenly hate), bribing someone with fruit snacks, breaking up sibling drama in the backseat, and praying no one wipes a snack-sticky hand on the dress you just steamed. All for that “perfect” family holiday photo.

Trust me, you’re far from alone. Most of my clients arrive with a hint of panic in their eyes, and by the end of our session? They’re laughing, relaxed, and amazed at the beautiful images we created together.

As a Chicago family photographer who’s photographed a lot of families through the joyful chaos that is the holiday season, I’ve got some tips to help turn your holiday portraits from stressful chore to festive memory.

Spoiler: it’s completely doable, and dare I say… even fun?

Let’s Be Honest: Holiday Photos Can Feel Like a Lot

Look, I get it. Between work, school schedules, dinners, dance class, and Target runs (because if you’re anything like me you forgot to bring your list and have to go back for something you forgot), adding a photo session to the mix can feel like one more thing on the never-ending to-do list.

But here’s my philosophy: family portraits shouldn’t feel like a burden. They should be a chance to slow down, connect, and actually enjoy being together.

Yes, even if your four-year-old insists on a sparkly Elsa dress and your husband only agreed to photos after serious negotiations. Especially then.

Let’s break down how we make it easy, relaxed, and dare I say – kind of magical.

How to Actually Enjoy Your Holiday Portrait Session

1. Book Early, Breathe Easier

The best gift you can give future you? Booking your holiday session in October. Not only do you get first dibs on ideal timing (golden light after school, anyone?) but you give yourself space to decide on outfits, prep the kids, and design those cards without sprinting toward a photo lab deadline.

These sessions fill up quickly – and nobody needs the added stress of last-minute scrambling.

2. Dress Real, Not Rigid

The age-old question: what do we wear?

My styling tip? Start with a neutral base (think cream, soft gray, or navy), then add texture and a holiday pop. Cozy knits, a velvet dress, maybe a warm plaid scarf – they photograph beautifully against our cozy indoor studio setup.

And no need to match head-to-toe. Coordinated styles create a much more natural feel. It’s less “everyone in red sweaters” and more “this group actually has personality.”

Worried about how outfits look on camera? During booking, I provide you with a session prep and style guide that will give you ideas, and if you want I can help you with options personalized to your family. It’s kind of my thing.

3. Prep Kids (and Yourself) for Success

Parents often worry their kids won’t sit still or smile on command. Guess what? I’m not expecting them to.

The key to smooth sessions isn’t perfect behavior – it’s thoughtful timing, snacks (bless Cheerios), and setting the tone for fun. That means scheduling during your child’s happiest time of day, having a favorite toy or comfort item nearby, and knowing that giggles, twirls, and occasional toddlers-on-the-run are part of the magic.

Pro tip: keep energy up without sugar crashes. Mini pre-session dance parties encouraged.

And if you’re feeling nervous about how you’ll look (so many women do), know this: I guide you through every pose, every angle. You’ll feel more confident than you thought possible.

4. Bring the Whole Crew (Yes, Even the Dog on Sundays)

Pets? 1000% welcome on Sundays. For a lot of Chicago families, they’re a part of your story.

If your dog is just gracing a few photos and needs constant attention (like mine!), bring a helper to take them for a walk while we focus on the rest of the crew. Treats and squeaky toys go a long way.

Some of my favorite sessions include wiggly pups, and yes – we capture their personality, too. (Drool and all.)

5. Let Go of “Perfect” and Embrace the Real

Here’s a little secret: the best moments always happen between the poses. Tight hugs, toddler giggles, the way a parent looks at their child when they don’t realize I’m still shooting.

That kind of stuff? It doesn’t come from rigid smiles. It comes from letting go and letting your family just be.

So if someone pulls a silly face, or the baby won’t let go of their lovey… don’t sweat it. That’s your family’s story right now – and it’s worth remembering exactly as it is.

Holiday Photos Should Feel Like a Gift, Not an Obligation

The holidays move fast. Like, one-minute-you’re-carving-a-turkey, next-minute-it’s-January fast. But your portraits? They stick around.

These images become part of your holiday cards, your living room wall, the keepsake album your kids flip through year after year.

Instead of dreading the chaos, you get to walk away with photos that mean something. Photos that show your love, your laughter, your connection – not just your matching outfits.

And the best part? You don’t have to figure it all out alone. I’ll walk you through the entire experience so you can show up, look amazing, and have the kind of family session that feels easy.

Let’s Make Some Holiday Magic Together

If you’ve been putting off your Chicago holiday family photos because the whole idea feels overwhelming – this was your sign.

Booking your session early means less stress, more fun, and images you’ll be obsessed with.Ready to turn this year’s portraits into a beautiful (and actually enjoyable) memory? Reach out here to reserve your session or get more information here. Let’s make some magic together, and yes – we will totally have snacks.