Your Complete Guide to the Best Holiday Family Photos Ever

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The holiday sneak attack is real. One minute, it’s the eve of the school year and you’ve only just realized that your children have outgrown all pants and shoes. The next, you’re on a hayride, hauling an absurd pile of pumpkins in a wagon across a field in the middle of nowhere. Then wham. You’re singing carols on the way to snag the perfect tree.  

Believe it or not, there’s another easy-to-neglect deadline tucked in there that tends to come in even speedier fashion: The holiday family portrait session. 

While it’s already peak season for professional snaps in your cutest, most coordinated wardrobes, don’t sweat it just yet. There’s still plenty of time to book a sesh. 

So, deep breaths. Then check out our ultimate guide to taking the best family photos (possibly ever!) with tips from the pros (and parents) themselves. They’re sharing insight on everything from finding your perfect photographer match to choosing the best non-matchy-matchy get-ups, down to what to do once that digital gallery arrives in your inbox. 

Camila Montanhani, a lifestyle photographer in Montrose, New York, says the first thing to do when you’re looking for a photographer is to check out their website. “Or,” she says, “go on their Instagram account and connect with them. You’ll want to make sure your visions align.” Word of mouth is a good start to finding a family photographer, she says, so ask around: Friends or people from your parents’ group with similar styles, at the PTA meeting or even social media are good places to start. And be sure to look specifically at their portrait style — just because someone is great with nature or architectural photography does not mean they’ll capture family photos in the way you want. 

Once you schedule an introductory call with a photographer, come prepared with a list of questions. Montanhani urges clear communication, peppering her potential clients with questions about what they’re dreaming up for the sessions. “When you pick up that picture in 20 years, how do you want it to make you feel?” she asks. Collect inspiration from Instagram or Pinterest to share with the photographer so everyone can be transparent about deliverables and expectations. 

Regarding COVID-19 precautions: this is also a good time to discuss masking if this is important to you. While photography can take place with social distancing, you may feel more comfortable if the photographer wears a mask. Outdoor sessions are also generally a less risky option for parents who are concerned.

Some photographers like Montanhani offer a range of sessions to address different budgets. Depending on where you live, a 20-minute mini session could start at around $250. From there, a typical session would average around about two hours or, the most expensive option, a full-day documentary style session. Based on availability, she also offers rush fees for edited, curated galleries within 48-hours.

Montanhani also advises placing all the details in writing. Her contracts include the whole scope, from the date, time, location, and payment down to the session length and type. A good photographer will check the weather leading up to your session, but consider building a back-up plan into your contract in case your session is rained out, or someone in your family catches a cold. 

It’s also important to know when to expect your images, especially if you have a looming holiday card deadline. Montanhani, for example, tells clients she’ll share a sneak peek within a few days. Two weeks from the session, she emails the client a complete gallery of images. 

The next step to pulling off a photo shoot is picking that idyllic location. Choosing a spot that’s a family favorite can make it an especially memorable occasion. But sometimes, it’s exciting to explore somewhere new. Either way, be sure to take the commute into consideration. A far-off destination can dampen your children’s moods, especially if they don’t like long car rides. 

“When choosing a location, some families like to go to their local park they always go to,” says Oakland, Calif. photographer Benedict Lassalle. Spots where kids are already comfortable and excited will often lead to the most natural, meaningful candids.

“Others like to change locations every time and rely on me to offer new suggestions,” she says. That’s why she keeps a running list of locations on hand for clients to choose from. So, if you’re unsure what the best spot may be for your shoot, ask the photographer for their advice. “This time of year, the fall colors are really nice at the park or botanical garden. The light at the beach is beautiful at the end of the day,” she notes. “I like to recommend some different locations that have some personality in a way.” 

Next, pick a good window of time for your family. Typically, outdoor photography should take place around either sunset or sunrise, when the light is soft and filterer. “Funny enough,” says Lassalle, “I notice that new parents like to take pictures in the morning. They are happy to shoot right after breakfast and everyone is in a good mood.” Consider naps, mealtime, travel time, and any other complications to the schedule.

Parents are good about packing light, non-messy snacks, but Lassalle also recommends toting along a few other items such as a blanket, ball, bike, or basket with a few simple toys. Think: aesthetically pleasing dolls, trucks, wooden animals, or stuffies that you won’t mind making an appearance in your photos. Those small touches will often make a photoshoot feel even more special! 

Speaking of aesthetics, we tapped Los Angeles stylist Merisa Libbey for a few tips on getting the family dressed for a photo shoot. “Neutrals are always a good way to go for family photos or various shades of the same color,” she says. “Like, the colors of the sunset, for instance. Incorporate some textures like a knitted sweater or movement from a flowy dress.” Avoid uncomfortable closures or anything that may make little ones fuss during the shoot.

If your children want some input on their outfits, lay out a few options and let them choose. Finally, Libbey says, don’t push perfection. “Let them play and have fun,” she says. “Every hair may not be in place, but their happiness and personality will shine through which translates so much better than stuffy, posed photos.”

Children’s commercial photographer Priscilla Gragg adds, “It might be a good idea to bring a backup outfit in case something happens to the first choice, but I usually tell my subjects to come camera ready.” Like Libbey, she advocates for a casual approach. “I’m okay if the clothes don’t look extremely perfect, like they have just been ironed. I like for them to look as natural as possible,” she says, adding that parents and children should dress in clothing that they feel confident in and allows them to move freely. 

Some children may take time to warm up to the environment and the photographer, says Gragg, who also created a holiday fundraiser for hospitalized children called The Portrait Project. “In that case I would start with the kids who are ready to go, or even with the parents to loosen them up a bit,” she says. “Then slowly, I start gathering all for the group shot. I never force. The less attention you give to the ones that don’t want to come to the group shot, the more he or she will want to participate. This is a trick I do with my own kids.” 

In other words: don’t stress out or worry about time. A good photographer will ease everyone into the process. 

“I’m talking constantly to my subjects, asking all sorts of questions, sometimes trying to slightly embarrass them if I feel they can be a good sport about it,” says Gragg. “You have to find a certain connection. Usually, I can just be super silly, and it works, but this one time, I was working with an 8-year-old girl and she was really holding it back. To be clear, I am totally cool if that is her personality, and she doesn’t want to smile, but I knew I could find something in her. Then I remembered learning from her mom that she loves reading books and learning new things. All I had to do was start asking about science and animal fun facts. That was it.”

No matter the time of year, make a plan for your images so they don’t go unseen. “I personally use Minted for holiday cards,” says Gragg. “They have great paper quality and I love their address assistant. All of the contacts are saved, and I don’t have to text my friends each year for their addresses.” Other card companies we like are Tiny Prints, Shutterstock, and Pinhole Press. You can choose the frills (rounded corners, fancy envelopes, gold foil) or keep it simple. Some of these companies will even address and send your cards, leaving you more time to enjoy the eggnog and holiday movies. And if you’re short on money or time, most drug stores like CVS or Walgreens will allow you to quickly print some off right in store. 

If you’re crafty, you can print your photos from MPix and have the kids help glue them onto pretty cardstock for a meaningful afternoon activity that keeps little hands busy.

“For loose prints, large prints, and photo books, I use Artifact Uprising,” Gragg says. “I love their paper quality and colors. At the end of the year, I like to print one photo book with the highlights of the past 12 months. It has become a tradition and my kids now treasure the little books so much.”