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After clashing badly in family pictures a couple of years ago, I’ve become quite skilled in over-planning our family photo outfits. Anything worth doing is worth overdoing.
Last year I planned our outfits three weeks in advance. My daughter wore no fewer than four different outfits (four combos made from 2 different dresses, a knit bonnet, and fluffy UGG Bailey boots), and my son wore two unique get-ups. We had plenty of cohesive looks, including the same beleaguered expression on our faces.
This year, I started planning our attire eight weeks in advance. Enough time to prepare for every possible scenario.
Lights. Camera. War. It’s family-picture time, baby.
Time to battle-plan for that magical shot: Smiling, cherub-cheeked children. Children not merely laughing, but frolicking, gaily in gold-dappled meadows of wildflowers or a forest glen. Festooned in frocks and frill from Soor Ploom or Rylee + Cru.
Yet despite planning for every contingency, I chucked it all out the window at the last minute and we all turned out in Old Navy.
My true sentence number 8: Make sure your family has a ready supply of Old Navy staples, because after over-planning your family photo shoot wardrobe, for your non-angelic, non-frolicking, non-joyous spouse and children, you’ll just turn up in a freshly laundered version of your everyday selves and everyone will smile the wider for it.

My husband wore an Old Navy polo. My son wore Old Navy twill pants and an Old Navy clearance shirt. My daughter wore a cotton-gauze dress from H&M (that she’s since re-worn three times).
And on their feet, my son wore a pair of Mikoleon boots I picked up on Mercari. My daughter wore a pair ankle of Old Navy ankle strap flats. (For wide feet, these are the best dressy girl’s shoes. My daughter wears these daily. I have ordered the next size up, but really, I want to get a case of them in every color.) And my husband: He wore a pair of his infamous tennis shoes that he painstakingly colors (sprays) black.

But really. In the end, comfortable feet are (damn near) frolicking feet.
Photography from Leah Rivera is amazing.