The Best Dresses for Family Photos + tips to pick your most flattering option!

Taking family photos can be such a nightmare, if I’m being totally honest. The pictures are usually great once you get them back– photographers can work some real magic. However, the actual session itself can be really challenging when kids aren’t interested in cooperating, the weather is too hot or too cold, or the outfits are uncomfortable. Thomas and Charles are the cutest kids alive (I may be biased), but taking photos with them is not without its challenges.

Best Dresses for Family Photos + tips to pick your most flattering option!

While it can be difficult to navigate kids’ attitudes, I’d argue that the worst part of family photos is not wrangling your kids but rather finally getting the gallery back and not liking how you look in the pictures. After all the effort it took to get your family to smile in photos, not loving how you look in them is so disappointing—especially when you’re paying a professional photographer!

One of the most asked questions I get on a regular basis is, “What should I wear for my upcoming family photos?” And as someone who poses for photos daily and shops for a living, I do think I’m a decent resource when it comes to this question. I’m also a mom to a very active almost-4-year-old who doesn’t love pictures, and an almost 8-month old as well. So, when I tell you I get it, I get it.

Thankfully, I’ve learned a few things over the last few years that help me make sure that I look and feel my best in our family pictures, regardless of how the rest of the evening goes. I’ve gotten one too many galleries back where I haven’t liked how I looked, including fall photos a couple years ago! Now, I know what I do like to wear and what I don’t for family photos.

These pictures are a couple years old, but they are STILL my favorite family photos EVER. (Although, I was actually pretty thrilled with our family beach photos last summer too!). We took photos with Charles this spring and I love those as well, but they were for an ad and felt a little more “made up” than usual. I’m hopeful that we can schedule some family photos this fall!

Dresses for Fall Family Photos

I always opt for dresses for family photoshoots since they are the most forgiving and flattering. The last time I wore anything that wasn’t a dress in family photos was for our engagement photos over 7 years ago! So, today I’m sharing the pretty and practical dresses for fall family photos. While I have a bunch of cute dresses in my closet, not all of them work well for family photos.

A cute mini dress may be the perfect option for a date night with Tommy. However, it probably won’t look as good with a toddler on my hip. It wouldn’t look good while sitting in the grass outside or while chasing Thomas and Charles down throughout the evening. However, a maxi dress will allow me to bend down to grab the boys. It’ll also allow me to sit in the grass without flashing anyone and still feels special.

Below, I’m going to share the things I think about when picking out a dress for family pictures and a handful of cute options I’m loving this season. I hope you find something that makes you feel beautiful AND allows you to function as a mom. Let me know if you end up ordering any of these dresses!

What to wear for fall family photos:

Sleeve length and dress length:

First, I wanted to share a couple tips about how I choose what I’m going to wear and show some examples of what worked vs. what I didn’t love.

Since having kids, I’ve learned that I prefer to wear a 3/4 sleeve for family photos. While I have toned arms, there are much more likely to be unflattering angles when wrangling a very active child when wearing cap sleeves or sleeveless options. Part of that is simply knowing what I find looks best on me and part of it is comfort.

Sleeves

If I do opt for a sleeveless or short-sleeved option, I’ll make sure the dress is on the longer side. For last year’s family fall photoshoot, I wore a gorgeous flutter-sleeved, knee length dress that I feel GREAT in for a night out, but I hated how it looked in the photoshoot. I was constantly worried about my booty hanging out and had to mess with the sleeves frequently, and I didn’t feel like it was a very flattering option once I got the photos back. Was it awful? No. Is it my favorite, and did I feel my best? Also no.

I think what I learned after wearing a short dress for my beach photos and loving it, was that I need to balance the top and bottom. If I go for a short dress, I want longer sleeves, like this dress below.

If I go for sleeveless or short sleeved, I want a longer dress, like I wore for Halloween a few years back.

So, when choosing your outfit, start to pay attention to how you feel in photos in various styles of dresses. A few weeks before photos, gather a few dresses and prop up your camera and take a bunch of photos in various dresses (I use the Lens Buddy app to auto snap photos – it’s easier than the phone camera timer). You’ll likely be able to tell how you FEEL in an option while pictures are being taken and be able to SEE how you look your best.

Shoes

This really depends on where you’re shooting the photos, the style of your dress and your personal preference. But I’ll share a few things to help you think through it.

If you’re taking photos on the beach, I’d go barefoot or wear simple sandals.

If you’re taking photos on grass, a trail or rocky area and really want to wear heels, bring a pair of flat sandals for walking in between locations and then slip your heels on when you get to each area. I did this for our maternity photoshoot and for both of our fall photoshoots and it worked well.

Since I’m so short (5’1″), I typically prefer heels, but I always bring two options and always choose a block heel option for easier walking and balance.

And if you’re wearing a very long dress that barely shows your feet, opt for a very neutral sandal so it will just kind of disappear.

Okay, now let’s get into some specific examples of dresses that I think would work well on most people!

Lyles Dress

I recently got this Lyles Dress in the bright red color from Tuckernuck. It’s hard to beat a maxi dress with a v-neck and removable tie waist. Anything that gives a dress a defined waist automatically makes it more flattering. While the red is definitely festive, this dress also comes in a chambray blue, which would be perfect for early fall. You can style this with flats, heels, or even boots.

If you’re pregnant, I think this would be gorgeous with a bump too!

Hazel Bouquet Corduroy Clifton Dress

Next up is a mini dress (and some thoughts on why I’d still wear it!). Like I mentioned at the beginning of this post, I prefer to wear maxi dresses when possible for family photos since they are easier around kids and feel special and “dressed up”. However this short Hazel Bouquet Corduroy Clifton dress meets my other requirement: sleeves. I think it’s important to have one or the other, at least.

I absolutely LOVE the fall floral pattern with the brown background. The only think I’d be worried about for this dress is the length, since I know I’ll have to bend down, squat, and sit in the grass for our photos. For that reason, I’d be sure to wear these tan-ish biker shorts from Amazon underneath so that I wouldn’t have to stress about flashing any passers by. I’d style this dress with brown booties or tall boots and have the guys wear navy and white.

Moon River Green Multi Midi Dress

This Green Multi Midi Dress by Moon River is a bit out of the ordinary from other dresses I go for, but I think it’s the perfect option for anyone hoping to disguise a bump or their stomach. The pattern is busy and distracting, the center ruching and asymmetric hemline make it fun and playful, and the colors are neutral enough to pair with your husband’s or kid’s outfits. The sleeves are feminine and fun, and the fit of the dress is super flattering. It looks so much more expensive than it is!

Hill House The Ellie Nap Dress

The best dress I own for almost any occasion is my Nap Dress from Hill House. Smocking is always a super flattering option because it’s form fitting and still comfortable, and the flutter sleeves are feminine and fun. You already know that the length is perfect for family photos too. I recently ordered the Navy Equestrian Toile colorway and it’s the perfect option for fall.

The Thea Twofer Sweater Dress

When I saw this Thea Twofer Sweater dress, my immediate thought was that it would be perfect for fall family photos. There are so many things to love about it! The long sleeves are important to me because I tend to feel insecure about how my arms look in photos when I wear certain things. I like the idea of being able to grab the boys, throw them into the air, and hold them all without worrying about if my arms look ok (but there’s a GREAT sleeveless option if you feel differently). I also love the maxi length of this dress because it feels dressy and special. I’ve found that while a maxi dress may seem “fancier” than a mini dress, they are actually so much easier to wear around kids because you’re never overthinking when you have to bend down!

The colorway is another reason I love this maxi. The olive green is such a great fall option and easy to style with plenty of other colors for your family. I think I’d style this dress with nude heeled sandals or clogs

The Somerset Maxi Dress

Next is the Somerset Maxi Dress from Anthropologie. You have the best of both worlds with a fall patterned floral and a tiered maxi that still somehow feels cool enough to wear in the south for “fall” photos. I love that you could easily tie in greens or pinks or reds with the rest of the family. And you’d get a ton of use out of this dress for church, parent events for your kid’s school, or a date night. I’d even wear this to a wedding if it was not a super formal affair!

Pair this with black heeled sandals and you’re golden.

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