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

Taking family photos can be such a nightmare, if we’re 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 is the cutest kid alive (I may be biased), but taking photos with him is not without its challenges.

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

And while it can be difficult to navigate kid’s attitudes, I’d argue to say that the worst part of family photos is not wrangling your kids, but rather it’s finally getting the gallery back and not liking how you look in the pictures. After all of 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-3-year-old who doesn’t love pictures. So, when I tell you I get it, I get it. Plus, my content manager also does photography on the side. So, between the two of us, I think we can help you out with some outfit ideas!!

Thankfully, I’ve learned a few things over the last few years. It helped 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 last fall’s pictures! 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 this summer too!)

Dresses for Fall Family Photos

I always opt for dresses for family photoshoots since I think 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 5 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 down throughout the evening. However a maxi dress will allow me to bend down to grab Thomas. 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 Thomas, 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 or messing with the sleeves 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 the beach photos and loving that, it was that I need to balance the top and bottom. If I go for a short dress, I want longer sleeves.

If I go for sleeveless or short sleeved, I want a longer dress, like I wore for Halloween last year.

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 a 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 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!

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 thomas, throw him into the air, and hold him 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.

Taupe Bellagio Knit Dress

I’ve never eyed a dress more in my life! Unfortunately I feel certain this Taupe Bellagio Knit Dress from Mirth will be too long on me (I’m 5’1″), but if you are taller than me, I hope you’ll consider wearing this gorgeous sweater dress for your family photos this fall. I love the idea of a more neutral toned theme! I’m a fan of this dress for similar reasons to the first: it has sleeves which help with any arm insecurities, and the length is super easy to wear while wrangling kids. You could style this with tall leather boots or opt for a dressier strappy heel.

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

Rosewood Chintz Crawford 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 long sleeves when possible for family photos since I’m never sure how I’ll feel about my arms in the pictures. However, some dresses are just worth the risk! This Rosewood Chintz Crawford Dress from Tuckernuck is one of those exceptions.

I absolutely LOVE the fall floral pattern, the brown background, and the flutter style short sleeves. 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 didn’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.

One note on this dress — since the waistline is totally relaxed, this is a great options for baby bumps or anyone who prefers to have more coverage or fabric in the stomach area. It may not be a good option for you if you’re easily bothered by the look of wide or oversized dresses.

Chambray Crosby Dress

I absolutely LOVE this Chambray Crosby dress, you guys. I already ordered it for myself! If you’re looking for something slightly more casual for your family pictures, I can’t think of a better option. It has sleeves (!), which makes the idea of a shorter length even easier to plan for. Sure, there’s not as much flexibility with chasing Thomas around in a mini dress, but I think this is worth it. I love the idea of the boys wearing navy and white, and pairing this dress with clogs like this pair from Madewell.

O.P.T. Tuscany Dress

If you’re planning to snap your family photos earlier this fall, I love the idea of this orangy-red smocked dress by o.p.t. 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 perfect for family photos too. Since the color is such a fun orangy-red, I might have the boys wear jeans and a white or navy shirt. I would stick to tan or nude sandals with this rather than trying to style it with fall shoes.

Exclusive Vintage Poppy Isabel Classic Dress

This red and pink long sleeve maxi dress is absolutely gorgeous. I would wear this in a heartbeat if I felt like this smocking style worked well for me. I find that dresses with a fully smocked top look better on smaller busts, and since I’m pregnant and that’s not the case for me right now, I have to pass. However, if you have a smaller chest, PLEASE order and wear this for family photos this fall! Imagine how pretty it would look with green grass in the background and your kids in light pink or red! Your husband could wear a white button down and jeans to make this look slightly more casual.

Green Smocked Amazon Maxi Dress

If you’re looking for a more affordable option, this maxi dress from Amazon is perfect. I love the high neck and flutter sleeves, and the olive green feels like a great neutral fall color to me. Your family could take this a few different directions: light pinks, navy, white, light greens and sage hues, or even tan. For $38, you can’t beat this!

Shop The Post