Planning My Family’s Outfits! | Boston Area Family Photographer

One of the many reasons I love booking photo sessions for my own family each year is that it reminds me what it’s like to be the client. Our annual family photos are coming up in just about a week, and figuring out what to wear has been another part-time job. I’ve ordered countless dresses for myself, and about a bajillion pairs of pants for my beanpole of a two-year-old. I finally have it all sorted out, and thought I’d share the process I used for picking our wardrobe!

First, I worked on MY outfit. Why? Because let’s be real- moms are hard on themselves and won’t be comfortable unless they’re wearing something they feel awesome in. I tried on about four other dresses before I settled on one I love. It’s burgundy, long, and imho, rather dreamy :). The boutique I got it from is called Cleobella, if anyone’s interested. And no, I didn’t pay full price ;). If you’re the kind of person who feels good in dresses, I definitely suggest them for photos. A long dress will give your hand a “job” (you can hold it!) and may provide some movement in your photos. If long dresses aren’t your jam, mid-length can look great as well. Stylin’ skinny jeans and a cute, textured top are also a great option.

After I figured out what I was going to wear, I worked on my son’s outfit. I found a shirt I loved pretty quickly from H and M. Check it out here. Finding pants was a bit of a fiasco, though. Being in the 90th percentile for height and 25th for weight, he’s kind of a twig. Typically, I don’t care if pants look baggy on him, but I definitely didn’t want that for photos. It took ordering 5 or 6 pair before I found what I wanted. Finally, I picked my husband’s outfit. He already owned a pair of camel-colored pants that I love, so all I had to do was find a shirt. I picked an off-white, long-sleeved Henley, and voila! Done!

The family below also spent time carefully planning their outfits, and mom shared her ideas with me prior to their session. The end result was perfect and worked so well for this adorable farm location in Winchester, Massachusetts (a location worth considering in the Boston area!).

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Melissa Rabbitt is a Boston area family photographer specializing in infants, toddlers, and young children. You can click here to reach out and learn more!


Oh hey! I’m Melissa, a Boston family & newborn photographer, but I like to refer to myself as a toddler-whispering, child-taming, photographic ninja.