Back to School Style

And just like that, Summer Break is over! We tried to savor every moment, but it still managed to fly by. But that’s life with kids, right?! One moment, they’re bald and squishy attached to your hip, and the next they’re moving out and have a much better head of hair.

Today Little Miss starts 8th grade, her final year in middle school, and for the first time in 13 years, I don’t have two kids posing with new backpacks on their first day. We’re moving our son to college later this week, a fact that pesky lump in my throat has reminded me of every day since last August!

But even though back-to-school looks a little different for us now, I couldn’t miss the chance to shoot my favorite post of the year…back-to-school with J.Crew Factory! These photos just mean a little more to me now.

Henley Shirt | Chino Shorts | Tie-Front Shirt | Quilted Vest | Skinny Jeans

Can you believe they were only 3 and 8 when I started this blog?! I feel equal parts elated for making it to this point, and devastated by how much our family life is changing.

But most of all, I’m just overwhelmingly grateful I get to love them, raise them, and have a front row seat to their lives.

When it’s time for back-to-school shopping, J.Crew Factory is always our first stop. The styles are more timeless than trendy, the materials soft, and the quality is spot-on. Plus, the prices are always budget-friendly with incredible sales. In fact, they’re having a one day only flash sale, and today everything is 50% off!

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!

Striped T-Shirt Dress | Camo Shirt | Pocket Tee | Chino Pants

Henley Shirt | Chino Shorts | Tie-Front Shirt | Quilted Vest | Skinny Jeans

These pocket tees are super soft, come in a slew of colors, and hold up great in the laundry. He has several in the heathered wash, as well.

Little Miss is sensitive to fabrics and textures, so she appreciates the soft cottons, smooth seams, and mostly-tagless pieces.

Striped T-Shirt Dress | Camo Shirt

Her tie-front tee is made of the softest jersey material, and comes in solids, stripes and camo. They are a great lightweight for layering into Fall, too.

Tie-Front Shirt | Quilted Vest

Henley Shirt | Chino Shorts

Pocket Tee | Chino Pants |  Striped T-Shirt Dress | Camo Shirt | Pocket Tee | Chino Pants

And just for fun…here’s a peek at our first back-to-school post with J.Crew Factory five years ago!

Eyelet Peplum TopLeopard Slides

This blog is (hopefully) a spot of inspiration for you, but it also serves as our own personal scrapbook, and I love that we’ve documented so much of their lives over the last 10 years. Thank you for embracing us, and supporting us through this journey of life, loss, joys, and parenting. I honestly feel like because of you, we’re not doing this alone.

Have your babies returned to school yet? Are you going through a new season of parenting, too? I miss their faces already and can’t wait to hear all the first day stories. Be kind to them, World, they’re our whole heart!

You can find these darling styles, and so many more, all 50% off today J.Crew Factory! I’m obsessed with these leopard pants and leopard sweater for me, and couldn’t grab this blazer fast enough!


*Photos by the darling and talented Mary Hafner. This post is created in collaboration with J.Crew Factory, but all product selections, styling, and proud mama hearts are my own. Thank you for supporting Hi Sugarplum sponsors!*

Leave a Comment


  1. Shay Shull wrote:

    I’m thinking about you this week, mama!! It’s going to be a great year for both of them! xo

    Posted 8.12.19 Reply
  2. The flashback made me want to BAWL. The way those two look at each other is too sweet.

    Posted 8.12.19 Reply
  3. Lori wrote:

    My how they have grown up! As much as you will miss your son, you will become even closer with your daughter! It’s a special time!

    Are you modeling for Amazon, now?
    You have probably seen this by now but just in case…

    Posted 8.12.19 Reply
    • Cassie wrote:

      I am excited for the time with her, and know we’ll grow even closer! And yes, I’ve seen that…they are using the photos without permission, unfortunately.

      Posted 8.12.19 Reply
  4. I love jcrew factory. The kids look great. You’re lucky that the kids will pose for the blog. Mine will not.

    Posted 8.12.19 Reply
    • Cassie wrote:

      I let them choose their own clothes, and pay them when it’s for a collaboration…so they feel like they have a say in it all! It’s always their choice to participate or not!

      Posted 8.12.19 Reply
  5. Michelle Nordstrom wrote:

    Back to school is always my favorite of your blog posts. I love seeing the love between them. She’s going to miss him so much. Thanks for sharing them with us.

    Posted 8.12.19 Reply
  6. Sandy wrote:

    Awwwwww! Little Miss’s eyes! The Teen! With a haircut!

    Posted 8.12.19 Reply
  7. Nedda wrote:

    They are so adorable! I’m sending my first child to school Wednesday (kindergarten), and I’m so nervous. I see him skipping ahead to college and i don’t think i can take it

    Posted 8.12.19 Reply
  8. Meghan G. wrote:

    I’m sure there were plenty of sibling squabbles through the years, but it’s pretty clear how much those two love each other! A clear reflection of the love and admiration between their parents. 🙂 It’ll be a tough week but hang in there! Mine are still in that early stage of life… 3 and 7. The days can be long but I know they’ll be grown and leaving for college way too soon as well!

    Posted 8.12.19 Reply
  9. Kerry wrote:

    Thinking about you! This is a new chapter. Praying that you feel the support from your blogger family. Your sweet kiddos are lucky to call you mom!

    Posted 8.13.19 Reply
  10. DS wrote:

    I remember it being such a difficult period sending our first off to college! Just as I thought things were getting easier, I would break down in tears! But as the holidays rolled around it felt as though everyone was more adjusted to our new routines and more settled! Hang in there momma ❤️

    Posted 8.24.19 Reply