A Fun School Dress Up Day Outfit 

My son wears uniforms at his elementary school daily.  But on the last Friday of each month, they have a dress up day celebration and it’s so cute to see the students arrive at school dressed in style.  Even the teachers get in on the fun and as if that wasn’t enough, there’s a pizza lunch and yummy treats involved! #signmeup In August, my little bestie shared the perfect school picture outfit idea with you guys.  This month, he is back to share an outfit idea that is great for dress up days at school, everyday fall wear, or even Thanksgiving.  

That said, let’s break down the whole look! 

Train Sweater

If I had to choose my very favorite store to shop at, I would hands down say Shein.  I love all the hidden treasure you can find on there that I don’t see anywhere else and as we all know, my son loves all things train.  He often says he wants to be a train engineer when he grows up so, when I spotted this adorable train sweater, I knew I hit the jackpot! It’s crazy soft, beautifully made, and so stinking cute with the raised, brushed train graphic.  The mix of blue, green, white, black not only work together to provide visual interest but make it super versatile.  It’s perfect worn on its own now and when the weather gets cooler, layered under a chunky knit cardigan or any jacket.  

A Fun School Dress Up Day Outfit Photo 2

White Jeans

For pants, my son’s train sweater will coordinate with lots of different style bottoms.  But, for a fun school dress up day look, you can’t go wrong with white jeans.  While it’s not as dressy as black jeans, in my opinion, it looks more pulled together than blue jeans.  I love how it gives his outfit a modern feel and the distressing is just right.  Needless to say, it’s such a pleasing color combo.  What’s more, these jeans are pull-on style which means there are no button or zipper to fuss with.  In other words, your little guy won’t feel constricted while enjoying a slice of pizza or two.  Because let’s be real, no one wants to be uncomfortable during a meal! 

A Fun School Dress Up Day Outfit Photo 3

Shoes

As for shoes, these ones are by Cat and Jack Glenn sneakers from Target and it’s the perfect shoe to complete my son’s school dress up day outfit! They are stylish, lightweight, and downright cute.  The zipper makes them easy to get off and on, and they do not require any breaking in.  My son found them super comfortable right out of the box and they stayed put through lots of running, jumping, and walking. #momwin  

A Fun School Dress Up Day Outfit Photo 4

On a different note, I know I sound like a broken record over here, but I really love October.  It’s such a fun month! Between the cooler weather, pumpkin-flavored food, fall festivities, and of course, spooky season, it’s hard not get swept up in all the excitement.  Eeek! Speaking of the countdown to Halloween is on, and we are so excited.  Our mommy and me Halloween costumes are ready and this year we went with a food theme! Any guesses?

Now it’s your turn! 

Do your kids have dress-up days at school? What are your Halloween plans? #dotell

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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).  

**Shopstyle currently doesn’t support the Shein website.  Therefore, I am unable to include this train sweater and white jeans in my widget below.  However, if you want the exact style, click the links above.  Additionally, Shein has many similar versions of this sweater so I have put together a list on the liketoknow.it app that you can check out for more options.

26 COMMENTS

  1. NancyC | 2nd Nov 23

    Love the train sweater–so fun! 🙂

  2. Shauna | 2nd Nov 23

    How cute! Love the sweater! Hope you guys had a great Halloween!

    Shauna

    http://www.lipglossandlace.net

  3. Jill | 1st Nov 23

    I love that the school has a dress up day so the kids can express their individuality and take a break from uniforms! Your son’s train sweater is super cute!

    Jill – Doused in Pink

  4. Laura Bambrick | 31st Oct 23

    I find so many good things for my girls from Shein too! That train sweater is the cutest!

  5. Anna | 31st Oct 23

    Your son looks super cute in this casual day clothes. Love all the pieces. Anna

  6. Carrie @ Curly Crafty Mom | 30th Oct 23

    Love the train! My son used to be crazy about them for years!

    Carrie
    curlycraftymom.com

  7. Marky Ramone Go | 29th Oct 23

    Dress-up day is a good way for kids to express their individuality as opposed to wearing school uniforms in the other days of the week.

  8. Kim Carberry | 27th Oct 23

    What fun to have a dress up day. My girls used to wear uniforms at school and they loved it when they could wear their own clothes.
    The train sweater is just adorable. I love Shein too and have only recently started using it and I’ve found some fantastic outfits.

  9. Jennifer Prince | 27th Oct 23

    Aw! That train sweater is so adorable. What child wouldn’t want to wear that? So cute!!

  10. Fransic verso | 25th Oct 23

    This look cool, love the color matchup of the outfit and the colors are pretty as well.

  11. Ntensibe Edgar | 25th Oct 23

    Aaaawwww….I love the sky blue colour train surrounding the train! It’s good to see something drawn on a car, in the era when words are more than the drawings.

  12. khoingn | The Broad Life | 25th Oct 23

    Wow, looks like your boy has a good outfit for the school. A good appearance will boost confidence for good school days surely.

  13. Rosey | 24th Oct 23

    The train sweater is so sweet. Perfect for a dress up day at school.

  14. Olga | 24th Oct 23

    A train sweater and white jeans are so cute! My son is in kindergarten, and his pants are always messy. So, white color isn’t for us now, but I adore this cute sweater.

  15. jess jannenga | 24th Oct 23

    HI Maureen
    Back from my trip and I trying to get caught up on commenting. Sorry I haven’t been great. You have always been wonderful commenting on my blog. Your son is so stylish! I am sure he would win if they gave out awards! This is an adorable sweater! My nephew when he was young loved trains too. YOur son is getting so tall and I love to see his little outfits. I love the white jeans with the sweater too.
    Hope you are doing well!
    jess xx
    http://www.elegantlydressedandstylish.com

  16. mireille | 24th Oct 23

    He’s a stylish cutie! Love the color of his sweater.
    http://www.chezmireillefashiontravelmom.com

  17. Sonia Seivwright | 24th Oct 23

    Your son is looking smart. I love the jumper, and the overall outfit colours blend in well.

  18. Melanie E | 24th Oct 23

    Oh wow, I really love the school dress up day outfit. I’m sensing a theme here as there is a train on the jumper and I’m sure he had a train Halloween costume so I’m guessing he’s a train fan. That looks like a fun and comfy outfit.

  19. Kathrine Eldridge | 24th Oct 23

    Love this cute sweater! I used to enjoy dressing my boys up for school for Halloween. We will just be handing out candy to all our neighbors for Halloween.

    https://www.kathrineeldridge.com

  20. knycx.journeying | 24th Oct 23

    A vibrant color and sweet outfit, that’s wonderful, and glad that you guys enjoyed it!
    Thanks for sharing!

  21. Ebony | 23rd Oct 23

    This is such a great outfit idea! My son loves trains, so I know he will love this outfit idea with the weather changing so soon! Ordering one today. Thanks for the great recommendation!

  22. Debbie | 23rd Oct 23

    How fun for the kids to wear something fun on dress up day. Your son looks very stylish in his train shirt and outfit. Great outfit pick!

  23. Stephanie | 23rd Oct 23

    What a great idea to take a break from the school uniforms! He looks adorable in this outfit – just love the entire ensemble.

  24. Beth | 23rd Oct 23

    He is the cutest model ever! I love the white jeans and shades!

  25. Stephanie | 23rd Oct 23

    We have dress-up days for special occasions, but my kids don’t have uniforms so they can wear just about anything. This week is Red Ribbon Week so they have themes for each day. Today is wear red and crazy hair, tomorrow is bright/neon colors, Wednesday is career/college day, Thursday is Western wear (we are in Texas!) and Friday is superhero day.

  26. Marysa | 23rd Oct 23

    That is great that they let the kids have these days to dress up in something other than a uniform. Sounds like it is a fun day overall. This is a great outfit!

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