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My suggestions - pick your own outfit first, then coordinate. Choose a few colours you want, maybe one bright one for a pop. Minimal patterns - maybe a fall-coloured plaid flannel for the 8 year old, but otherwise go with plain colours. And don’t forget shoes.

I think it would depend on the dress and the accessories. If it was a fancier dress I don’t think it would work with the overalls on the baby. If it’s more casual and you were going to pair it with boots and maybe a big necklace or a bright circle scarf that would work, I think? Where will the photos be taken?

@MoonMoon: depending how urban your location is, if you did collared shirt and a bow tie and rustic accessories for big brother and dad—button down and suspenders for big brother, vest or flat cap for dad?—overalls might work for LO, but I think you’re swimming upstream. I agree that starting with your outfit is probably best to set the tone for the family overall. You want everyone to look like they’re going the same place.

Coincidentally, we’re doing family photos next week and I pulled outfits today. I’m between two sets, one is a little dressier and has a navy and cream maxi dress for me, blue sweater and pants for DH and a pinky purple dress and cream sweater knit leggings for DD (who is almost 2). The other is casual with a yellow sweater and jeans for me, maroon sweater and jeans for DH and white shirt, purple leggings and denim jacket for DD. We’ll be in a community garden at peak foliage, otherwise I wouldn’t have gone for maroon/yellow/purple, but with the setting i think it would work and we’ll all have blue denim to tie it together.

Have you done any googling to find things you like? The navy-blue-pink idea was straight from our photographer’s blog.

If you like the plaid flannel idea, I'd get older son that, and then coordinate off his colors.
I like the khaki plaid at old navy, https://oldnavy.gap.com/browse/product.do?pid=737542102&pcid=999&vid=1&searchText=boys+flannel#pdp-page-content

and then I'd get youngest a solid color shirt that matches - possibly this one in mesa rock: https://oldnavy.gap.com/browse/product.do?pid=738179012&cid=37045&pcid=37045&vid=1&nav=expmore%3Atoddler%20girls%3Ashop%20by%20size%3Atoddler%20boys%2012m-6t&cpos=20&cexp=2223&kcid=CategoryIDs%3D37045&cvar=16846&ctype=Listing&cpid=res21100506802823443805251#pdp-page-content

A navy blue maxi dress would then work for you, and maybe jeans and an off-white or mustard for DH?

Could also use the black/white plaid for older son, black maxi for you, maybe a white shirt for LO with bibs, and grey for DH?

For our family photos I picked a patterned floral dress for DD, and then the rest of us wore a solid color that matched, we ended up with dark blue, mustard, and autumn red.