Boston Fall Family Photos guide – tips for success

It’s Boston Fall family photos season! If you’re like me, you’re obsessing over what everyone is going to wear and worrying about whether your kids will cooperate. If not, I need your zen tips because even I do this. After years of photographing families, I have a few tips for prepping to help set you up for success for your Boston Fall family photos.

Boston Fall family photos

What should I wear to my Boston Fall Family Photos

*Check out my Pinterest to see some outfit inspiration!*

Generally, I suggest you style yourself (assuming mom is reading this) and then style everyone else around you. If you have a particular outfit you want your kid to wear, then style everyone around them! Think “going together” rather than “matching.” I like to pick 3-4 colors and mix up the shades. Depending on the day, the weather might be a little chilly, so don’t forget about layers for the little ones and even picking out a cute knit hat or jacket if your session is later in the year.

For moms, I have a client closet with lots of dresses that are bump friendly for maternity sessions, and mostly size mediums with elastic waists to accommodate a range of sizes. As you can see, I love creams, tans, browns, rusts, etc. My personal preference is texture over prints and these warm neutrals, but these are YOUR photos, so if this isn’t your style, that’s totally cool! If you want to buy something yourself, I love Baltic Born, Free People, and Vici. I’ve even found great options at Target and Old Navy. If you’d rather a more casual look, jeans and a sweater are great too. As for shoes, wear something cute and comfortable and I’d avoid heels as we’ll be walking on grass, but know they will definitely not be a focus.

What should the rest of the family wear for Boston Fall family photos

For dads, I personally prefer sweaters and t-shirts (I am obsessed with henleys) over collared shirts and button downs, and texture over stripes or prints. Jeans or khakis are great, as are colored chinos. I’d avoid anything super dressy–no need to wear a suit or tie to your Boston Fall family photos

For babies and kids, I love Quincy Mae and Rylee + Cru if you want to get something special, Zara and H&M have lots of cute options, but honestly Target’s Cat & Jack brand and Old Navy has tons of great options. I love sweaters, waffle, and rib knit for texture, and layers to keep little ones warm. If baby isn’t walking yet and it isn’t too cold, leave the socks and shoes in the car and we can get some cute photos of their little piggies.

Boston Fall family photos

Getting your kid to smile

Don’t worry about telling your kids to smile. Your job is to smile, look at your kids, your partner, or me. Don’t make funny faces at them to laugh and point at my camera, unless you want a bunch of photos of you making weird faces and pointing. 

Don’t practice saying “cheese” before the session. Tell your little one that we will be playing together and having a good time while the nice lady takes photos. If you want genuine smiles, this is going to come from fun interactions. PLEASE PLEASE PLEASE do not stand next to me yelling your baby’s name over and over and clapping. They will likely get over-stimulated and have a zombie face with a weird fake smile staring off into the distance and I will get a headache.

Trust me. This is why you are hiring me. I’ll play with your little one to get them to laugh, and give you prompts to do the same. Let me do my job, and you’ll all have fun!

We’ll get photos of everyone looking at the camera, but more of everyone having fun together. I know everyone wants the perfect family portrait for their holiday card, and WE WILL DO THAT, but the photos you’ll want on your walls will likely be the genuine interactions with each other. 

Boston Fall family photos

Prepping before the Boston Fall family photos

While you don’t need to practice smiling, there’s one big thing you should do to prepare: feed your kids. Avoid a hangry meltdown by giving them a meal before you come, feeding them snacks in the car on the way, and bringing extra snacks just in case. I know it might not line up with your typical schedule, but trust me.

The other thing is trying to get your kid to nap. I don’t even want to put this here because we all know that the one day you need your kid to nap, they are not going to, but try to adjust the nap so they aren’t exhausted by our session. If you have a little one who usually wakes from their last nap at 3 and goes to bed at 6, and our session is at 7, push the nap later. I’m sure you’d rather have a cranky afternoon than a meltdown photo session. 

Boston Fall family photos


I’m totally here for bribes, especially for toddlers. Bring some M&Ms or cheddar bunnies or whatever else your kiddo is into. I find this works best specifically for sibling shots–“I’ll give you an M&M if you hold your brother in your lap while I count to 10!”–rather that smile for an M&M 100 times. Our sessions are about an hour long, so try not to bring them out too early or you could have a battle over the bag of yogurt snacks the entire time (speaking from recent experience). 

Boston Fall family photos

Binkeys/Toys at Boston Fall family photos

Try to leave them in the car. If they don’t have access to them, there won’t be a battle over them the entire time.

Boston Fall family photos


I occasionally get asked if a grandparent or family member can come to help. iIf you want to bring someone to help with the logistics of getting everyone ready, that’s cool. I’m also totally fine having them hop in for photos as well. But PLEASE PLEASE PLEASE ask them not to yell your kids name over and over behind me. You’ll get the same outcome as above but you will also be annoyed.

Boston Fall family photos

PhotographyWhitney O'Brien

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Whitney O'Brien is a Boston newborn photographer with a studio in Dedham, MA. She specializes in natural, timeless portraits of motherhood, including maternity, newborn, milestone, and family sessions.


She serves Boston neighborhoods such as Roslindale, Jamaica Plain, West Roxbury, and Hyde Park, as well as Dedham, Needham, Newton, Brookline, Westwood, Norwood, Walpole and beyond.


To see my latest work and photos of my own kids, follow me on social media!