Holiday Style for the Whole Family

Have you recovered from the Black Friday/Cyber Monday mania yet? That was definitely a whirlwind, but I hope my posts helped to take some of the stress out of your holiday shopping. Now to find a hiding spot for all the orders that are about to start flooding in! #amIright?!

We have some pretty clever snoops in our house, so it’s always a challenge to keep things secret! Is it the same in your house?

Today I’m excited to share more festive holiday styles…this time, for the whole family!

J.Crew Factory Holiday Style

Our entire family adores J.Crew Factory styles, fit, and soft fabrics, so it’s my go-to for affordable preppy styles, and the best range of sizes for the kids. But I especially like it when I’m dressing the family together. Their colors and patterns mix beautifully across Women, Men, and Kids, making it so easy to coordinate us all.

The starting point for this year’s holiday style was my darling plaid skirt (on sale!)! It was love at first sight for me, and I built the rest of the outfits around it.

Sugarplum Style Tip: Plaids are a great base pattern because of all the color options! This plaid has black, blue, green, red, and yellow! That’s a lot to work with!

J.Crew Factory Holiday Style Plaid
Shawl Sweater | Plaid Shirt | Red Sweater | Plaid Skirt | Dog Sweater | Plaid Skirt | Men’s Blazer | Fair Isle Scarf

Dog Sweater | Plaid Skirt | Chain Bracelet | Similar Necklace | Stud Earrings

From there, I chose pieces that played up each person’s personality, and stayed true to their individual styles. While I’d love for Little Miss to wear these darling glitter boots…Converse are more her style. Same with the teen…he’s never not wearing ripped jeans.

The photos represent who they truly are in this phase of life, and that’s what I want to remember years from now!

Sugarplum Style Tip: Allow your kids to infuse their own styles and have a say in what they’re wearing for family photos. They’re a lot happier on-camera when they feel good in their clothes!

Little Miss chose the adorable dog sweater, which is perfect with skirts or jeans. And even more importantly for her, super soft with no scratchy tags!

These two make my heart want to burst!!  Please world, be kind and look after them!!

J.Crew Factory Holiday Style Dog Sweater
Shawl Sweater | Plaid Shirt | Dog Sweater | Plaid Skirt

My skirt is a crisp cotton in all the perfect colors of the holiday, and the sash can tie at the front or back. I’ll add black tights once the weather cools even more.

Fit Tip: The skirt runs large, so size down one. I’m wearing 00.

Plaid Skirt with Tie | Red Sweater | Chain Bracelet

Our son surpassed the boy’s sizes a few years ago, but he’s still really slim…so we love the broad selection of sizes at J.Crew Factory (starts at 28-waist!).

They also make some of my favorite coats, and I love that they apply the same high-style to the kids, too.

Girls Faux-Fur Trim Coat | Women’s Faux-Fur Trim Coat (love this one, too!)

Shawl Sweater | Plaid Shirt | Dog Sweater | Plaid Skirt

Mr. SP loves the slim fit of the blazers and sports coats, and prefers to dress them down with denim. He’s not much of a scarf guy, but admitted this fleece-lined fair isle was warm and soft.

Red Sweater | Plaid Skirt | Similar Necklace | Faux-Fur Trim Coat | Men’s Blazer | Fair Isle Scarf

Girls Faux-Fur Trim Coat | Women’s Faux-Fur Trim Coat

This year marks 25 Christmases with this guy…how is that even possible?! I’m grateful for him every day. Even the days he makes crazy.

Red Sweater | Plaid Skirt | Similar Necklace | Stud EarringsMen’s Blazer | Fair Isle Scarf

And hard as I try, I can’t help but think this is our ‘last’ full holiday season together. This time next year, our son will be away at college! I know, I know…he’ll come home, and of course be here for Christmas, but it will still be different. It’s made me really embrace this season, and we have a lot of family fun planned!

The Dallas Symphony is always at the top of our list, and I know exactly what we’ll all be wearing! If you’re still dressing your family for the season, you’re in luck because J.Crew Factory is 50% off all full-priced items today (no code needed, priced as marked)! So many adorable finds for every person in your family! Happy Christmas, lovebugs!

[Shop Our Holiday Styles]



*Photos by the darling Audrie Dollins. This post created in collaboration with J.Crew Factory, but all styles, clothing & grateful heart are my own. Thank you for supporting Hi Sugarplum sponsors.*



Leave a Comment


  1. Shay Shull wrote:

    You post great pics all the time, but these are seriously THE BEST PICTURES YOU’VE EVER POSTED! They’re stunning, Cassie!

    Posted 11.28.18 Reply
  2. Sheaffer wrote:

    These picture are DARLING! Y’all are just so cute! And you need to stop the college talk right now. #stopit #rightnow #seriously

    Posted 11.28.18 Reply
  3. Sandy wrote:

    Great style and pics! And Little Miss-those eyes!!

    Posted 11.28.18 Reply
  4. Sevahn wrote:

    Bursting with joy! These photos spell JOY.

    Posted 11.28.18 Reply
  5. What a gorgeous family! I just love this post!

    Posted 11.28.18 Reply
  6. Kim wrote:

    That last picture is perfection. What a lovely family.

    Posted 11.29.18 Reply
  7. Kathy wrote:

    Your family is just so darn cute!! What great pictures!!

    Posted 11.29.18 Reply
  8. Kathy wrote:

    These photos are beautiful!! Your family is just so darn cute!!

    Posted 11.29.18 Reply