Tips for Styling Holiday Family Photos

Happy Thanksgiving week, friends! The kids are home all week, and we’re so ready to spend some quality downtime together, and take a break from schedules and routines. We’re road-tripping to a few college campuses for the first part of the week, then plan on hunkering down with turkey, pie and decorating! What are your plans?

Also on my agenda this week is creating our annual Christmas card (Minted is my favorite resource for gorgeous card designs and customer service), and since we just got our family photos back, I’m excited to get started! Today I’m sharing our photos, along with my best tips and ideas for styling and shooting family photos. And if you’ve been following me for awhile (I’ve been blogging almost 8 years!), you might be shocked to see how much the kids have grown this year! #gulp

Once again, I turned to J.Crew Factory to plan our family outfits (see a few from years past here, here, and here). It’s the easiest spot I’ve found to effortlessly coordinate the entire family, in the styles we each love. The colors and patterns are right up my preppy-loving alley, and the styles are more timeless than trendy. Not to mention, the prices are budget-friendly and they have amazing sales. In fact, everything is HALF OFF!!

This year we went the classic route with traditional plaid, accented by grays, green and blue. Little Miss and I fell for this plaid skirt and ruffle blouse, so they became the catalysts for the family outfits.

On Her: Jean Jacket | White Tee | Plaid Skirt | Pearl Headband
On Him: Half-Zip Sweater | White Shirt | Khaki Chinos

On Mr. SP: V-Neck Sweater | Striped Oxford
On Me: Plaid Ruffle Shirt | Wool Pencil Skirt | Similar Leopard Heels | Crystal Necklace | Chain Bracelet | Earrings

Fit Tip: Both the shirt and skirt run true, and I’m wearing an XS shirt and 0 skirt (it’s fully lined!).

On Mr. SP: V-Neck Sweater | Striped Oxford
On Me: Plaid Ruffle Shirt | Wool Pencil Skirt | Similar Leopard Heels | Crystal Necklace | Chain Bracelet | Earrings

Puppy Update: Miss Mollie has seamlessly become part of our family, and we’re all completely in love! Having two is so fun, and easier than I’d feared. Mollie just follows Maggie’s lead, so training has gone so much easier. And Mollie wants to play constantly, so Maggie is acting like a puppy again. 

She sleeps in the Laundry Room, and the accidents are happening less and less. #hallelujah And she loves to snuggle in your arms like a baby, so Little Miss loves that! She’s also found her voice, and it’s so funny to hear a deep rasp come out of her little body. 

On Her: Jean Jacket | White Tee | Plaid Skirt | Pearl Headband
On Him: Half-Zip Sweater | White Shirt | Khaki Chinos

Fit Tip: Little Miss is extra-sensitive to fabrics and tags, so we really appreciate the softness and quality of J.Crew Factory’s pieces. She especially loves their long-sleeve tees. And you moms of teenage boys will be thrilled to know the Men start at size 28 waist, and have extra-long inseams! Our son loves their jeans and khaki pants.

Tips for Styling Holiday Family Photos

Determine the feel of the photo and card you want…do you want a theme, festive, everyday, seasonal?  From there, choose outfits that make sense in that setting. Remember seasonal props might be fun, but if you plan on displaying the pictures year-round in your home, you might not want to be wearing Santa hats.

Consider your photo location and background. What you wear should somewhat reflect your environment, and the colors should be visible.

Start with a single piece and build around it. If you fall in love with a skirt for your little girl (Little Miss loved this one), or a shirt for yourself (like I did this one!), use that as your base, and build from there.

To keep us coordinated, I think of the family as one single outfit, as opposed to four individual ones. If you can interchange items between outfits, then they work as a whole. You want the people to shine, not the uniformity of the group.

Shopping a single store, like J.Crew Factory, makes mixing-and-matching for the whole family a lot easier, since the color palettes usually coordinate across departments.

Choose outfits that reflect each person’s style, and give them a say in what they wear. They’ll be a lot more relaxed if they feel like themselves (and aren’t wearing scratchy fabrics!).

Don’t shy away from pattern, as it adds interest and layers to your photos, just be sure to vary the scales.

Skip the graphics and characters. You want the focus to be faces, not clothes.

Have a plan before you drag everyone in, so husbands kids don’t grow weary before you even get started. And remember to stay calm (and flexible!)…your attitude will set the mood for the rest of the family. (We actually arrived at my original location choice, only to find a full-blown festival in progress! We had to switch gears completely and find a new spot.)

Outfits don’t come together overnight, so allow yourself plenty of time before the shoot. No matter how many deep breaths you take, if you come to the shoot frazzled, it will show in your body language.

And just for kicks…here was our family just five years ago (wearing J.Crew Factory, no less!!). Can you even believe the change?!

holiday family photo

Don’t expect to get the shot in one take either…we literally shoot over 100 to capture the right few. And if all else fails, bribe your family with treats after!

But most importantly, have fun! The idea is to capture your family’s dynamic, not create the ‘perfect photo.’ People will notice the joy on your kid’s faces, not their outfit. And if the whole thing is too overwhelming, just have everyone wear what’s most comfortable, and take the photos in black and white!

Have you taken family photos this year? What tips do you have to ensure a fun, successful shoot? Although, the mishaps and outtakes are usually my favorites! Don’t forget everything at J.Crew Factory is half-off today, and click here for a chance to win their $500 gift card sweepstakes!

{Shop the Parents Style}

{Shop the Kid’s Style}


*Photos by the darling and talented Mary Summers. This post is created in collaboration with J.Crew Factory, but all styles, opinions, and grateful heart are my own. Thank you for supporting Hi Sugarplum sponsors.*

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