Cold Weather Family Photos with Toddlers: How to Prepare Your Child for a Chilly Session

If you’ve ever shown up to a family photo session thinking, “It doesn’t feel THAT cold…” only to realize five minutes in that the wind has other plans—this one’s for you.

This family session at Retzer Nature Center is the perfect example of why I always say: don’t let the forecast scare you away. These Retzer Nature Center photos may look warm, cozy, and full of smiles—but what you don’t see is that it was a chilly 40 degrees and, just to keep things interesting, it started drizzling halfway through the session.

And yet? The kids absolutely crushed it.

We photographed for less than 20 minutes, the children held it together like champs, and we walked away with a surprising amount of variety. This is the magic of keeping things short, flexible, and fun—especially when you’re working with small kiddos and cold weather photos.

As a Wisconsin family photographer (and a mom of toddlers myself), I promise: cold-weather family sessions can be wonderful with just a little prep. Here’s how to set your kids up for success.

Why I Love Chilly Family Sessions (Yes, Really)

Cold-weather sessions have a quieter, more peaceful feel. Fewer crowds, softer light, and kiddos naturally leaning into their parents for warmth—which creates the sweetest, most natural moments. At Retzer Nature Center, the muted tones of late fall paired beautifully with this family’s connection, even with gray skies and mist rolling in.

And remember: your cold weather family photo session doesn’t need to be long to be meaningful. Short sessions often work better for toddlers, especially in chilly conditions.

5 Tips to Prepare Your Child for a Cold Weather Family Photo Session

1. Dress Smart: Warm First, Cute Second

I always tell parents this: warmth matters more than anything. Cold kids don’t smile—they survive.

Layer up with:

• Thermal or long-sleeve base layers

• Sweaters or cozy knits

• Jackets or coats we can remove briefly for photos

• Warm socks and closed-toe shoes

Pro tip: Neutral coats or textured layers photograph beautifully, especially for cold weather photos.

2. Explain What to Expect (In Toddler Language)

A simple heads-up goes a long way. Before the session, tell your child:
“We’re going to take pictures outside. It might feel chilly, but we’ll be quick and you’ll get lots of snuggles.”

Setting expectations helps avoid that surprise meltdown when they step outside and realize it’s cold.

3. Bring a Warm-Up Break Item

For this Retzer Nature Center session, parents brought coats and blankets that were just off-camera. Between quick bursts of photos, kids got bundled back up.

Other great warm-up helpers:

• A favorite blanket

• Hand warmers (for parents holding little hands)

• A warm drink for after the session

We move fast, warm up often, and keep things playful.

4. Trust a Short Session

This entire session lasted under 20 minutes—and that was intentional.

When it’s cold (and especially when it starts drizzling), less is more. Toddlers have a limited tolerance window, and pushing past it rarely results in better photos.

Short sessions =
✔️ happier kids
✔️ less stress
✔️ more genuine smiles

And I promise, we can still get plenty of variety in a short amount of time.

5. Let Go of “Perfect”

Wind-blown hair. Rosy cheeks. Extra snuggles. A little chaos.

This is real life—and it’s beautiful.

Some of my favorite images from this session happened when the kids were being held tight, wrapped up, or laughing through the drizzle. Cold weather photos aren’t about perfection; they’re about connection.

The Result? Cozy, Connected, and Worth It

Even with chilly temps and light rain, this family leaned in, trusted the process, and showed up ready to have fun. The kids did amazing, the parents stayed relaxed, and Retzer Nature Center photos delivered exactly what it always does—natural beauty and a calm backdrop that lets families shine.

If you’re considering a cold-weather family session and feeling nervous, let this be your sign: you don’t need perfect weather. You just need a short plan, warm layers, and a willingness to embrace the season you’re in.

Because one day, you’ll look back at these photos and remember not how cold it was—but how close you all felt 🤍

If you’re dreaming up your own cold weather photos and wondering if it’s worth it, I promise: it is.

Location: Retzer Nature Center

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