The Perfect School Picture Day Outfit

Now that school is back in session, picture day is right around the corner! I know many of you are still on the hunt for a cute outfit for your little guy.  If that’s you, you’ve come to the right place.  Today, my little bestie is sharing an outfit idea that is perfect for your son’s picture day or even dress up days at school.  

Let’s start things off with this adorable gingham shirt!  

Gingham Shirt

I love the way my son looks in a button-up shirt and this gingham top from Amazon is adorable.  Not only is the gingham pattern such a fun print but it adds the right amount of oomph for that school picture day vibe.  And, because the material is made of 100% cotton poplin blend, this shirt is incredibly soft, well-made, and lightweight.  So, even though, it has long sleeve, your little guy can totally wear this now.  But you can choose to roll the sleeves up like we did for added style and versatility.  Of course, when the weather gets cooler later, he can easily throw on a cardigan or a denim jacket to stay warm.  To top it all off, this gingham shirt comes in many colors, but I went with the green and white color combo because it complimented my son’s outgoing personality.  

Gingham Shirt with Yellow Shorts and White Shoes Photo

Shorts

While you can wear any bottom with this style of shirt, I thought I’d choose some shorts to coordinate with my son’s button-up top.  This yellow pair from the Children’s Place was a no brainer.  It adds visual interest while keeping his outfit cohesive.  Plus, they are comfy and lightweight.  And as if that wasn’t enough, it comes with an optional belt and the waistband on this short are adjustable which is great if your son is on the slimmer side and petite like mine.  #momwin I appreciate that he can easily run around and play at school without feeling restricted or constantly having to pull up his pants.  But if you want to take it down a notch, you can certainly swap out the bright colored shorts for jeans for a more muted look.  

The Perfect School Picture Day Outfit Photo

Shoes

When it comes to shoes, my son loves easy and simple.  So, I am always looking for comfortable shoes that can be taken on and off easily.  These white ones from Target check all the boxes.  I love that they are slip-ons and don’t require any laces to be tied or straps to fuss with.  He’s had these for over a year, and they are incredibly comfortable.  Bonus: they are washable!

The Perfect School Picture Day Outfit Photo

On a different note, it’s crazy to think that summer break is almost over and that my son’s first day of school is in five days including today.  He’s starting 4th grade this year and it’s safe to say, I am having all the mama feels.  I personally love having my son at home with me and while I am excited about the coming school year, I can’t deny that it’s also bittersweet to see my little guy becoming not so little anymore.  Seriously, like how did that happen? #timeisathief

The Perfect School Picture Day Outfit Photo

What grade will your little one be going into this year? Do you plan a school picture day outfit like we do?

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*Disclosure: This post contains affiliate links.  If you click through and make a purchase, I may receive a commission (at no additional cost to you).  

**Additionally, some items linked above are not the exact item shown because it is either old or sold out, but I linked similar items for those that are unavailable.  

25 COMMENTS

  1. Lyosha | 5th Sep 23

    love the colors! nice choice. I love the green shirt

  2. Mica - Away From The Blue | 2nd Sep 23

    That is such a cute outfit on your son! it’s nice that your son is able to pick whatever he wants to wear for picture day. The kids still have to wear school uniform on picture day here!

    Thanks for joining the Weekday Wear Link up 🙂

  3. Samantha Laycock | 31st Aug 23

    Such a cute outfit! Time goes by so fast. By the time pictures come here, we are wearing warmer clothes.

  4. Sangeetha | 28th Aug 23

    The outfit idea for school picture day is spot on – the gingham shirt and shorts combo is both stylish and age-appropriate. It’s great to see such thoughtful suggestions for dressing up little ones. and Thanks for the links!

  5. Neely Moldovan | 27th Aug 23

    What a cool kid! He looks so cute!

  6. Fransic verso | 26th Aug 23

    This is cool, the color combination is nice as well. Hope you are well and wish you good times in the school days.

  7. Kathrine Eldridge | 25th Aug 23

    He is such a cutie in this first day of school look! The contrasts of colors is so nice. He is growing up so fast!

    https://www.kathrineeldridge.com

  8. Catherine Shane Cabuhat Rojo | 24th Aug 23

    That’s a nice outfit, he looks so cool! I’ll definitely check those because it looks comfy as well!

  9. Ntensibe Edgar | 23rd Aug 23

    Hhhhmmm….I love the shirt so much. It’s not a colour that will draw in so much heat. We will all be fine. The flipflops are a favourite of mine, too!

  10. Lanae Bond | 23rd Aug 23

    That is a cute and comfortable look you created.

  11. Marysa | 23rd Aug 23

    I love this outfit! Classic and not too busy, but bright and fun! Looking good.

  12. Caroline | 22nd Aug 23

    The Gingham Shirt looks great on your son, and the yellow shorts pair nicely with it. My kid also loves comfortable shoes, and I’d choose the same white color as well.

  13. Alita | 22nd Aug 23

    I love that button-up top. It looks comfy and indeed perfect for a school picture day.

  14. beth | 22nd Aug 23

    Im so sad that summer break is almost over! I wanted to spend more time with mynkids! Also, this is indeed the perfect school picture day outfit.

  15. Nelly | 22nd Aug 23

    That shirt and the shorts are so cute! I have to get this for my little nephew ♥️

  16. Monidipa | 22nd Aug 23

    Loved your tips on creating the ideal school picture day outfit! Your advice on blending comfort, style, and confidence is spot-on. The outfit ideas you shared are not only trendy but also practical for nailing that perfect snapshot. Great job!

  17. Heather | 22nd Aug 23

    Great timing for this school pic post! I love the happy clothing colors and the happy kid too.

  18. Melanie E | 22nd Aug 23

    That certainly is a great outfit for little ones. Your son looks very happy and relaxed in it. I’m sure my son being around a similar age would like that too as he is very much into shirts. The shoes sound great. Slip ons can be easier to wear.

  19. Richard Lowe | 22nd Aug 23

    Great pictures! It’s crazy how fast they grow and how quickly time flies.

  20. Stephanie | 21st Aug 23

    This is such a cute outfit! I love my boys in a button-up shirt for picture day, too. We just can’t wear green since they use a green screen for the photos. I’ll have to see if it’s made in blue as that looks best on my boys and works with the green screen used.

  21. Debbie | 21st Aug 23

    I hope your little guy has a great school year! He looks handsome in his picture day outfit!

  22. Bojana | 21st Aug 23

    He looks so handsome, as always! Is he/you excited for another school year? Did you enjoy your summer together? I can’t believe he is going into 4th grade! This is such a big transition from little kid to more big kid, by the end of the year you’ll really notice that change. It’s a good change but hard to think about on the mama heart. What doe back-to-school mean for you?

    bosbodaciousblog.blogspot.ca

  23. Jill | 17th Aug 23

    My daughter just graduated from college so I’m feeling nostalgic and really miss picking out picture day outfits. Your son looks so cute! It’s the perfect picture-day look!

    Jill – Doused in Pink

  24. mireille | 17th Aug 23

    My kids know I won’t buy the school pictures and only a year book at the end of middle school and last two year of high school so we don’t dress up for picture day. But I do love seeing how other do! My oldest is a senior so we had senior pics in a tux done (all of them do) and I surprised my son with actually ordered a few pics, lol! He looked so good!
    http://www.chezmireillefashiontravelmom.com

  25. Kathrine Eldridge | 17th Aug 23

    Your son is getting so big! I adore this look for his first day of school. He is one cool dude! My youngest is starting his last year of high and my oldest is starting his last year of college. Where did the time go?

    https://www.kathrineeldridge.com

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