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Back to School Outfits: Part One

I almost just made a slideshow of back to school sweatpants. But in NYC our numbers have stayed low (fingers crossed) so it seems as if our kids will be starting school in some very modified form next month. So I figured I would put together my annual shopping list. If you’re new here, I have a skillset/disease where I look and look for the the most perfect items. It’s sometimes exhausting to live in my brain but the result is lots of curated items I can share.

My general shopping strategy tends to be affordable basics and neutral color palettes for clothes. Then we do more colorful items for accessories and shoes and backpacks. I splurge on good quality outerwear.


A. Colorful beanies are a staple in our house. They really make the outfit. (I also love the Uniqlo cashmere beanies but they aren’t out for the season yet.)
B. My boys have been dressing in this brown on brown tonal look. It looks so good! I’ve been buying pretty much everything I can get my hands on in this color.
C. I’m really picky about stripes and this one is solid.
D. Accidentally happened upon this colorful calendar and fell in love.
E. Fjallraven backpacks, overpriced but we still keep buying them.
F. I look for the slim fit chinos and but several. (My kids don’t wear many jeans.)
G. I love Vejas. It’s like the French version of the Converse.


A. These are a MUST because half the time we’re going to be doing distance learning. I prefer the zoom calls remain on headphones.
B. Go Sports! Do the thing that wins the point! This is my favorite basketball! (They also make soccer balls and pretty much everything else too!)
C. These are low maintenance no-wrinkle shirts. I love a nice button up on a little person.
D. I used to have a backpack JUST LIKE THIS. It still holds up.
E. This notepad comes with built in pencils!
F. More slim fit chinos. My kids roll them up with the no sock look.
G. Tie-dye socks. Cause its 2020 and they’re having a moment.
H. Comfy sports shoes!


A. Dennis the Menace vibez.
B. My kids have figured out whenever they wear these spinny hats people give them candy.
C. Darts! They seem safe, what could go wrong?
D. Cute lighting graphic tee!
E. This long sleeve shirt is great for layering and faded to perfection.
F. Shorts while the warm weather lasts.
G. I bought this hilarious nose pencil sharpener for my kids and they’re obsessed.
H. My oldest kids are old enough to easily tie their shoes but I swear its sometimes nice to be able just have some slip ons for crazy mornings where you got to get out of the house quick.


A. Chambray shirt!
B. We usually give our kids a pencil case with personalized pencils (see the next item) at breakfast on their first day of school.
C. Personalized Pencils are my favorite tradition. Here is my favorite source. (The website is annoying but they ship very quick!)
D. I discovered this tiffin brand while traveling in Thailand and bought one for each kid for lunch boxes. They’re really great and stack easy and come in a ton of colors.
E. Quilted backpacks! These are so cool.
F. My kids have been super into chess so I bought this set and it is GORGEOUS! On sale!
G. I buy these slim fit pants in bulk.
H. My favorite alarm clock!
I. Classic high tops. They look so good with pretty much every outfit.


A. Their friend Marlowe always shows up wearing this cool neon hat.
B. Remember before when I said I keep buying clothes in this color!
C. Hang Loose – I love a simple tee.
D. I like my backpacks colorful to distract from all the homework.
E. Our favorite water bottles.
F. I love how these pants hang–I got the kids a few pairs.
G. More tie-dye. More problems.
H. Birks! while the weather lasts.


A. I LOVE a red beanie.
B. Another back to school tradition we have is iron on letters. The kids get to pick what they want their sweatshirts to say. Mine is going to say GO JOE + KAMALA.
C. My kids love these vintage throw back games.
D. We usually buy a few basics like this for layering.
E. Penny Boards are so cute and come in so many good colors.
F. I’ve seen a bunch of brands make a waterproof-ish short. I really like them!
G. I love these simple velcro shoes.


A. It’s a SIGN!
B. I love shirts like this that are *slightly* fancier than a t shirt.
C. This backpack is a cutie.
D. Record Player – My kids have been collecting records. It’s fun to go to the store to pick out a new one.
E. I love the cut of these plaid pants.
F. My kids JUST discovered Hamilton and this has been on repeat all summer.
G. Stan Smith Adidas are so cute. Love the velcro version for my youngest.

Stay tuned for Part Two.

  1. Sarah

    August 13, 2020

    These are great picks! Is it okay that I also want to wear everything posted above? 🥰

      • Maria
      • August 13, 2020

      I just bought that stripe shirt from look one last week for my 38 year old self! The largest size in boys is a solid Xs/s in Womens in Zara.

        • jordan
        • August 20, 2020


  2. Britt

    August 13, 2020

    I cannot overstate how much I love this return. And “/disease” 😂

  3. June

    August 13, 2020

    These are adorable!! I love each theme and you picked great items for each collection. You should do a series on adult clothes.

  4. Zoe

    August 13, 2020

    The only thing I can think to say to adequately describe this is “amaze-balls”

    High. FIVE!!!!!

  5. Amy

    August 13, 2020

    Love this! Hope there will also be Simone inspired options! And echo the request for adult outfits above!

  6. Megan

    August 13, 2020

    I agree, please do an adult one!

  7. Rachel

    August 13, 2020

    These are great! I really really really really appreciate that it’s not just girls stuff and that it’s not a bunch of super hero silly graphic tees.

  8. Andrea

    August 13, 2020

    Thank you for the big selection of cute boys items for back to school! As a mom of 3 boys it is so helpful!

  9. Amanda Zhang

    August 14, 2020

    I’m 30 years old and find myself loving the look of velcro shoes! I wish all the ones in this post came in adult sizes!

  10. Emily

    August 14, 2020

    I love this guide! I can’t wait to get Personalized pencils for my son’s birthday. He’s found a love of comic book drawing, so he will
    Lose his mind over pencils to create! Always love your recommendations, so happy you’re blogging again.

  11. Claire

    August 14, 2020

    I’ve missed OHD. Welcome back!

  12. Emily

    August 14, 2020

    Welcome back!

  13. sandeep

    August 15, 2020

    thanks and sir u wrote very useful content for all

  14. no makeup

    August 15, 2020

    I miss school so much.

  15. Amy

    August 16, 2020

    I’ve been following you since before Moses was born, and I have to say I love seeing you back here. I think your ideas and personality are really what made the Oh Happy Day brand successful. I really appreciate the time and effort you are putting back into it, and I’m excited to see more!

      • jordan
      • August 20, 2020

      Thanks Amy! Feels good to be back.

  16. Parti Malzemeleri

    August 18, 2020

    thanks you this share, best redards

  17. sandeep

    August 19, 2020

    thanks your content is very awesome

  18. abhinav

    August 24, 2020

    1) It takes 700 gallons of water to make a cotton shirt. …
    2) The average American throws out about 82 pounds of textile waste per year. …
    3) Clothes can take up to 40 years to decompose. …
    4) Shoes can take up to 1,000 years to break down. …
    5) 95% of textiles can be recycled.

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