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.*

Leave a Comment

29 Comments

  1. You have such a beautiful family. Everyone looks so smart in their outfits! 🙂

    Charmaine Ng | Architecture & Lifestyle Blog
    http://charmainenyw.com

    Posted 11.20.17 Reply
    • Cassie wrote:

      Thank you so much! The one time a year I get to dress everyone how I want! 😉

      Posted 11.20.17 Reply
  2. Colleen wrote:

    Beautiful family. I cannot get over how much your son seems to have grown just this year. It looks like he is the same height as your husband or maybe an inch or so taller. Time flies!

    Posted 11.20.17 Reply
    • Cassie wrote:

      I think he looks different every morning when he comes down the stairs!!! How does it happen so fast?!?!

      Posted 11.20.17 Reply
  3. DC wrote:

    Would you mind sharing sizing info for your skirt and shirt? Beautiful photos!

    Posted 11.20.17 Reply
    • Cassie wrote:

      Yes ma’am!! Both are true, I’m wearing an XS shirt and a size 0 skirt (it’s fully lined).

      Posted 11.20.17 Reply
  4. Sandy wrote:

    Oh, my! Too many great shots, better do a photo montage! The ones of Sis and Bro sitting on the stone fences or bridge-keepers! And of course, all of you w/the dogs included. Luv the one of Dad w/”puppy blue eyes”. Lovely, lovely family photos!
    Off to check out the J Crew Sale-buy!

    Posted 11.20.17 Reply
    • Cassie wrote:

      Thank you, Sandy!! I was so happy with how they turned out!! Their faces melt me! xo

      Posted 11.20.17 Reply
  5. Awwwwwwwww! These are beautiful!!!! So many great shots, and the flashback made me want to bawl.

    Posted 11.20.17 Reply
  6. Jennifer wrote:

    What a beautiful family! I love the plaid and how it all coordinates!

    Posted 11.20.17 Reply
    • Cassie wrote:

      Thank you, thank you!! Happy Thanksgiving, Jennifer!

      Posted 11.20.17 Reply
  7. Heidi Ferguson wrote:

    Beautiful job! Love how everyone is coordinated but not cheesy, matchy matchy! Thanks for your practical & helpful hints!

    Posted 11.20.17 Reply
    • Cassie wrote:

      Thanks, Heidi!! I hope they were helpful tips!! I love styling all of us! xo

      Posted 11.20.17 Reply
  8. Ann Rea Miller wrote:

    I love your photos! You have a gorgeous family. Can you please let me know how the size of your plaid shirt runs? Thank you!

    Posted 11.20.17 Reply
    • Cassie wrote:

      Thank you, Ann! And yes, the shirt runs true…I’m in an XS!

      Posted 11.20.17 Reply
  9. Sandra wrote:

    Stunning family photos. I love the colours/coordinating you did. You are truly blessed Cassie. I also love your new fur baby!

    Posted 11.20.17 Reply
    • Cassie wrote:

      Thank you so much, Sandra!! I am blessed indeed, and so grateful for this family! xo

      Posted 11.20.17 Reply
  10. C.B. wrote:

    What a change from 5 years ago. You have a great looking family (the new puppy is so precious!!!). I have to say, I have never taken family photos in my life (it’s just not a thing in French Canadian families for some reason). In fact, I’ve never really felt the need to do it. But my boyfriend is an Ontarian (different province, different culture) and that’s definitely a thing for them (and English Canadians generally). It’s our first “official” Christmas together and he’s got two kids and always did family pictures with his ex (their mother)…….and now I feel like maybe we should do this (his family might expect it)…..a shoot like yours would definitely be more natural for me to do than what’s normally done here (posed pictures in front of a generic background at a photographer’s office). But then again, it’s already winter here…..too cold to shoot outside without heavy winter gear.

    Posted 11.20.17 Reply
    • Cassie wrote:

      Family pics are so fun to have as everyone grows and changes!! I don’t think you’d regret having them!!

      Posted 11.20.17 Reply
  11. Sharon wrote:

    You have such a beautiful family! I just love your new puppy and I love how you coordinated your outfits.
    http://www.forthewonderer.com

    Posted 11.20.17 Reply
    • Cassie wrote:

      Thank you so much, Sharon! Happy Thanksgiving to you and yours!

      Posted 11.20.17 Reply
  12. Jane wrote:

    Just lovely pictures. I love looking at the “old” and the “new”.

    Posted 11.20.17 Reply
    • Cassie wrote:

      Thank you!! So fun to see how much they’ve changed so quickly!!

      Posted 11.20.17 Reply
  13. Judy Clark wrote:

    Cassie,
    You do have a beautiful family. I love the the little plaid skirt and will order it for my little Granddaughter! I forgot where you got the boots for her. Would you mind sharing that info.

    Happy Thanksgiving!
    Judy

    Posted 11.21.17 Reply
    • Cassie wrote:

      Thanks so much, Judy!! Her leopard booties are from H&M! xo

      Posted 11.22.17 Reply
  14. Patti wrote:

    While your family looks fab, your 4 legged children steal every picture…especially that blue eyed funny little puppy! Question: what happened to the Home tab at top of your banner? So easy to find and read your latest post. All those categories are nice, but that Home tab was so easy. BTW, been following you since you redid your kitchen in your other home😊

    Posted 11.28.17 Reply
    • Cassie wrote:

      We had to temporarily take it down to make room for the Christmas Shop! But it will be back after the holidays! You can also click my blog logo to take you back to the home page anytime!! xo

      Posted 11.30.17 Reply
      • Patti wrote:

        Thank you so much, shoulda been able to figure that out myself😕

        Posted 12.4.17 Reply