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. I’m determined to slow the pace of our holiday, and enjoy the process, as opposed to running around like a crazy lady. Well, the crazy lady part is unavoidable, but hopefully I can limit the running around part. 😉

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 my best tips and ideas for styling and shooting family photos.

Once again, I turned to J.Crew Factory to plan our family outfits (see a few from years past 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 50% off through tomorrow!

Tips for Styling & Taking 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. 
* 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 frenzied, it will show in your body language.
* Start with a single piece and build around it. If you fall in love with a dress for your little girl (Little Miss loved this one), or a sweater for yourself (like I did this one!), use that as your base, and build from there.
* A good rule of thumb is to choose all cool tones (blues, red, grays, purples), or all warm tones (yellows, oranges, khakis, olives). This will keep everyone coordinated, but not matchy-matchy. You want the person to shine, not the uniformity of the group.

Fit Tip: You moms of teenage boys will be thrilled to know J.Crew Factory starts at size 28 waist, and has extra-long inseams! Our son loves their jeans and khaki pants.

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

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

* Choose outfits that reflect each person’s style (even if it’s kitten ears!), and give them a say in what they wear. They’ll be a lot more relaxed if they feel like themselves…or maybe just a cleaner, more stylish version. 😉

* Don’t shy away from pattern, as it adds interest and layers to your photos. To keep us coordinated, I think of the family as one giant outfit, as opposed to four individual ones.

* Lay the outfits out ahead of time, even take a picture to see how they’ll photograph together.

* Keep the looks more classic than trendy, so they don’t become dated when hanging in your home.

* Layering clothes adds texture and dimension to your photos. For instance, add a sweater or jacket for the guys, and accessories and cardigans for the girls. Remember the Rule of Three, and add that extra piece to give each outfit the finishing touch.

* Skip the graphics and characters.

* 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.

* Don’t expect to get the shot in one take…we literally shoot over 100 to capture the right few. And like I tell the kids, ‘The hammier you feel, the better the photo!’

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! 

Looking for more inspiration, or just a fun morning out?! I’m thrilled to be hosting a grand-opening event for the new J.Crew Mercantile store at the Shops of Preston Ridge in Frisco! (It’s behind Gloria’s, across from Stonebriar Mall.) Mercantile is essentially the best of J.Crew Factory, but in a shopping center setting, as opposed to an outlet mall. They also carry Mens, Women’s Petite sizing, and Crew Cuts for the kids…all at Factory prices!

I’ll be sharing some darling holiday looks, along with my top picks from this year’s Gift Guide. I’d love to see you, and chat all things cute and preppy while nibbling on breakfast treats, so I hope you’ll stop by and say hi!

{Shop Our Outfits All 50% OFF!}

{More Holiday Combinations}

*This post is created in collaboration with J.Crew Factory, but all clothes, ideas, and overwhelming gratitude are my own. Thank you for supporting Hi Sugarplum sponsors!*

Leave a Comment


  1. The tips are great, and the pictures are GORGEOUS! They capture your family so perfectly! I loved this post!!!!

    Posted 11.21.16 Reply
  2. Christina wrote:

    These are great tips and you have such a sweet family! We are taking our picture Thanksgiving out at my parents in the country.

    Posted 11.21.16 Reply
  3. Jenny wrote:

    LOVE the cat ears! That's totally something my daughter would wear! Also love the pup in the photos. Great photos!


    Posted 11.21.16 Reply
  4. Gorgeous! Love that Maggie dog is in them too!!

    Posted 11.21.16 Reply
  5. Those JEANS, Cassie!!!!! They flatter (not that you need any help) and fit you like a glove! Wowzahs!!!!!!!!

    Posted 11.21.16 Reply
  6. Joanne wrote:

    Love the pink that touches every outfit. It adds a cheerfulness to a fall landscape. That and your beaming smiles.

    Posted 11.21.16 Reply
  7. The most adorable family pictures!! You can just see the love and fun you all have. Happy Holidays!

    Posted 11.21.16 Reply
  8. Vel Criste wrote:

    Love all the tips Cassie and might I just say, you have a very lovely family! HAve a wonderful Thanksgiving!

    Posted 11.21.16 Reply
  9. Amy wrote:

    Your family is just darling! You always put a smile on my face! Have a wonderful week home with your kiddos!

    Posted 11.22.16 Reply
  10. I absolutely love that you let Sloan where the glitter kitten ears!! And I wholeheartedly agree…for me to stay calm and not get upset or rattled when things get a little off or when my husband huffs about moving on to one more location makes all the difference!

    Posted 11.22.16 Reply
  11. Kristen wrote:

    These photos are so great! I think the piggy back picture is my favorite. 🙂

    Posted 11.22.16 Reply
  12. The bits of pink in this color combo is just fantastic! I love this collection of outfits for photos!

    Posted 11.22.16 Reply