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Back to School Shopping for Boys

We’ve been traveling so much this summer that I knew we weren’t going to have time to do any of our back-to-school shopping when we returned. So this year I did it all online. I have a serious problem where I can’t spend money on something unless I think it’s the best. “The best” means lots of things to me. But I usually buy something because it’s cute, it’s affordable, and it’s good quality. If I drew a venn diagram then all the things I try to buy would be right where those three things intersect. You might be thinking “what’s the serious problem?” It only becomes a problem when I won’t just buy whatever socks are on the shelf at Target. Sometimes I’ll spend three hours searching stores for the best socks and still come home empty handed. As a result I usually do a ton of research. I’ll get stuck on a random thing like researching “the best looking shoes without laces” (there are a few years there where they don’t know how to tie their shoes yet and there aren’t a ton of good options.)

I thought I would share it here in case anybody is still doing their back to school shopping. In some ways I think it is more difficult to find good options for boys than it is for girls because there is less of a selection. I try to buy lots of basics in a neutral palate so the kids can get dressed themselves and it still looks good. I do little pops of color but for the most part I buy greys, navy, and nuetrals. I still try to dress the kids a little bit European-ish if you can call it that. Blame it on the time we spent living in France but I love me some monochromatic grey kids clothes. The boys still don’t have strong opinions in choosing their clothes so besides a few Star Wars t-shirts I usually pick out most things and they don’t care as long as it’s comfortable. I should mention that we live in San Francisco so our climate is very moderate year-round (we don’t do shorts or heavy winter gear)…

Back to School Shopping for Boys | Oh Happy Day!

Outfit 1

Sweater – I randomly bought this sweater from the Gap last year when Mos was attending a school with uniforms. I was shocked when I saw at the end of the year how well it held up. It’s thick but not too heavy, perfect on it’s own or for layering. This year I picked up a couple for each of the boys (they come in a few colors.)

Collarless Shirt – When we lived in Paris this style of shirt was common. I like that it feels European and because it’s slightly “fancier” than a regular shirt but isn’t a full blown button down. H&M carries this style a lot.

Pants – I like to throw in a little pattern like camo (or stripes) that feels like a neutral.

Fjallraven – These waterproof bags from Sweden are a classic in Scandinavia. They come in the best colors and you can get them on Amazon or in a ton of hipster-ish stores.

Bensimon High Tops  – These are great looking shoes. This is a French brand that you can find on Amazon. We get compliments on these where ever we go. They are durable yet comfortable and come in the best colors. The boys usually wear these if they are dressing up a little or we bring these along when we travel. Bensimon also makes a slip on but I don’t think they are as good looking as these laced high tops.

Back to School Shopping for Boys | Oh Happy Day!

Outfit 2

Sweater – In San Francisco we layer a lot so I stock up on these types of thin sweaters and sweatshirts. Most days my kids don’t leave the house without one. I usually pick up one or two every time I go to H&M.

Henley – This is another basic that has details that make it feel slightly nicer than your average t-shirt but casual enough you can wear to playtime at school.

Pants – I’ve been buying lots of these soft pants lately. The cut has a dropcrotch which make them feel stylish but they are so comfortable to wear. The kids love them and have been choosing them over their jeans.

Lunch Bag – I’m not impressed with the lunchbag selections out there. I looked everywhere and there was slim pickings. Moses chose this monster one from JCrew (it’s so great!). We’ve been using these metal LunchBots for a few years and we love them. It’s a little bit of an investment to buy them but ours are going on strong after two years. I like them because they are a bento-ish but they only have one lid so it’s easy for a kid to access. I learned early on I had to make lunch really simple or my kids would get distracted and choose recess instead of eating lunch.

New Balance – Every year I buy one pair of New Balance or Sauconys. They are really good looking and have a lot of support for day to day playtime. They come in lots of great colors but I gotta say JCrew always has the best selection though you can find a few other more simple options online. The velcro in the classic style can be harder to find. These are the main day-to-day shoes for my kids.

Back to School Shopping for Boys | Oh Happy Day!

Outfit 3

Tshirt – Whenever we see cute t-shirts at craft fairs or stores we pick them up. This Golden Gate Park bison tshirt is from Park Life. We also have lots of basic t-shirts around for layering. In the winter they never take off their sweaters so I try not to spend a lot of money since no one ever sees them! (I usually just source the basics from H&M or American Apparel.)

Skinny Jeans – I usually buy jeans in grey just because it goes with the whole neutral palate we have going on. H&M has good stuff in nice cuts.

Uniqlo Jacket – Uniqlo makes thin puffy jackets which are warm but not too bulky. This is a great winter layer over a sweater since it never gets super cold in the Bay Area.

New Balance – The velcro styles can be harder to find. They give lots of support and last a long time (I can usually get 5-7 months of hard play out of them.)

Back to School Shopping for Boys | Oh Happy Day!

Outfit 4

Hat – Cute accessories are the best part of dressing little kids!

Herschel – I really like Herschel backpacks. They have a classic look, they come in great colors and they are modern (they usually have soft pockets for laptops.)

Cardigans – I always buy a ton of cardigans. Mostly because they LOOK SO CUTE. H&M and Zara always have good options. If I want one with a pop of color Crewcuts always has great colors. I usually pick one up if they are having a sale.

Superga – Like I mentioned a lot of the velcro shoes aren’t very good looking but I think the Superga’s are really nice. This is an Italian brand that you can get on Amazon. It’s a nice basic tennis shoe that comes in good colors and the quality is great.

Back to School Shopping for Boys | Oh Happy Day!

Outfit 5

Mabo Basics – I got a bunch of these Mabo basics last year and my kids have worn them out and they still look great. They are organic and really high quality. I always put my kids in these when we travel or have a long flight because they are soft and comfortable.

Pants – Just more of these soft pants (I bought a bunch.) They’re sweatpants parading as regular clothes.

Bensimon High Tops – These aren’t everyday shoes for my kids but since they don’t look as used they can totally pass for “nice” shoes for a party or church.

Personalized pencils – I love buying school supplies! This year I’m surprising them with personalized pencils.

Fjallraven – Another Fjallraven (see above.)

Back to School Shopping for Boys | Oh Happy Day!

Back to School Shopping for Boys | Oh Happy Day!

Outfit 6

Socks! – Here is my secret for socks. Every year I choose one style of sock for each child and buy 15 pairs. That way if one ever gets lost they always have a mate. Also, think of how much time a year I save sorting socks! It’s kind of boring but it totally works for us. Gap is my favorite for socks. I’ve tried lots of brands and they last the longest.

Star Wars Sweatshirts – I try to keep their clothes free of brands but they always end up with a few Minecraft or Starwars things. (My kids don’t care, I know some children are super opinionated about this.)

Corduroy pants  – I always buy a lot of cords because they are soft but durable.

Vans – I love Vans because they look so classic and are easy to put on. These are also another great day-to-day shoe. They come in great colors (I still love the classic black and white check.) And the kids can run around in them easily.

Herschel – Another Herschel (see above.)

Back to School Shopping for Boys | Oh Happy Day!

  1. jody

    August 7, 2015

    genius list!

  2. Taylor

    August 7, 2015

    I love every single choice you made!

    I do the exact same thing when I shop–sometimes it slows down the process, but it results in living with things I absolutely love, finding better deals and saving my family money, and never having to return anything.

    Little boys’ clothes are the cutest. Thank you for posting everything–it can be hard to know how to search for exactly what’s in my head, and you just saved me hours :).

    Hope your boys have a fabulous first week back!

    PS–I’ve been reading for years but rarely comment. Just wanted to say thanks for all the quality content, bright and clever ideas, and generally mood-lifting joy. I love your writing style and your taste!

  3. terri

    August 7, 2015

    love the lineup!!…especially the paperwink pencils!! they are the best!!

  4. Angela

    August 7, 2015

    I’m always a little more flexible with “the best” when it comes to kid stuff. My girls’ school requires them to wear white polo shirts every day. Their first year at the school I spent a huge amount of time researching white polo shirts to find the ones that were going to stand up to a year’s worth of wear and tear. The ones I found were more expensive, but the reviews were great. They were sure to last. I was so proud of myself. Then on the first day of school, the school principal gave everyone “happy first day of school” red popsicles that no amount of stain treatment could get out. From that point on, I’ve bought the super cheap ones and just buy a lot expecting that they won’t last too long.

    I totally do the same sock trick as you for my kids – I have saved myself many, many hours of sock matching that way. I buy the same style for each girl, but put a colored dot on the toe with permanent marker to indicate who it belongs to. It makes my life so much easier.

  5. Cherie

    August 7, 2015

    The sock tip is genius!! So all their socks are exactly the same? And you don’t have to pair them up, you can just throw them in the drawer and the kid just grabs two when getting dressed? That’s brilliant. Even my two year old would be able to sort the socks if there were only two patterns to choose from!!

  6. Emily

    August 7, 2015

    I love this post- could you share the details on the orange eyeball backpack?

      • jordan
      • August 7, 2015

      The one I shared was actually a lunchbox, but they make backpacks too. You can find them here:

  7. Vanessa

    August 7, 2015

    Thank you for this awesome list! My son is going into Kindergarten and I had just bought the Fjallraven backpack last night after a whole day of research. You have made the rest of my back to school shopping a breeze 🙂

  8. Nicoletta

    August 7, 2015

    Oh boy… your first paragraph just totally described my “problem”! HA! This is exactly how I end up wasting waaaaaay too much time online shopping and not actually buying anything! Obsession!!!

  9. Paige

    August 7, 2015

    I love the outfits that you put together! The fifth one is my favorite!


  10. Nicole Ossola

    August 7, 2015

    Jordan, thank you for sharing this! I had never heard of Mabo and had forgotten that H&M now sells online. I have a four-year-old and we have had really good luck with Zara (those soft pants are the BEST!); I especially like their Mao-collared shirts. Another favorite of ours (very similar to Mabo in style for little boys!) is WHEAT, although they don’t show much selection online- their flagship store is here in Annapolis, MD and we are very lucky! We’ve also done really well with Petit Bateau’s clearance sale. It’s very tough to find good boy stuff, so please consider doing this again next year or for spring!

  11. Leslie

    August 7, 2015

    I know you don’t have girls but I would love to read a post like this for girls!!! I have two girls so I’m navigating those waters when it comes to back-to-school but I will file this post away when my newborn baby boy gets a little older (I’m so clueless about boy things obviously). Thank you for all the work and research you put into this!

  12. Elle

    August 8, 2015

    This list is awesome! Thank you so much for sharing. This inspired me to start shopping on-line for my two little girls. Too bad H&M doesn’t have on-line shopping for Canadians:(

  13. Stacy K.

    August 8, 2015

    I do this too! For the kids I don’t even have yet…. Ha! Seriously an issue.
    Anyway. Loved this post!

  14. Kamisha

    August 9, 2015

    Love this. My boys are five and seven.
    Do you use the Fjallraven Kanken mini or daypack for school? Just trying to figure out which would be better for sizing?

  15. joanna goddard

    August 9, 2015

    LOVE THIS. jordan, you are the best at this kind of thing!!!!

  16. shelley

    August 9, 2015

    fantastic post. I loved pouring over every detail. you are so great at what you do. please don’t ever stop blogging.

  17. kim

    August 11, 2015

    I too obsess about buying just the right thing, even though sometimes it drives me crazy. I figure that it’s best to have exactly what you want, rather then spend money on something that will do. I don’t like branded clothing either, for the most part (the occasional star wars or mickey mouse sneaks in), and my kids have all the same coloured socks each – with four kids, it saves tons of time when folding the washing, and also means they can always find a pair of socks themselves. Love these posts – thanks Jordan! 🙂

  18. Miranda Anderson

    August 13, 2015

    Thank you for making my back to school shopping a breeze. I love your style, so might just click+buy down the list!


  19. Kathy

    August 13, 2015

    These posts just make me smile. You have such a fresh and friendly style. Thanks for being so generous with your resources!


  20. OMG these are the cutest little boys outfits I’ve ever seen. I always thought I dressed my son well but I don’t come close to this … super trendy, but comfy, etc. Great picks!

    xoxo – Erin

  21. Maddy

    August 17, 2015

    Loved this, especially the shoe recommendations! That’s where I’ve had trouble finding not gaudy, good shoes! Thanks!

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