Our Favorite Back to School Looks for Boys


We are affiliate partners with Rockets of Awesome.

It’s back to school season, but in Northern California, back to school shopping can be tricky. Personally, I like to get a first day of school outfit, then pause until the weather starts to change a bit.  

Although it still feels like summer, it’s a good time to start checking out the new collections because there is a chance by the time it actually feels like fall the styles you love might be on sale!

Here are my favorite picks for boys this season!

Rockets of Awesome

Rockets of AwesomeWe have been using Rockets of Awesome for years with my daughter, but my son was not big enough until now. This season, we just received his first box and he LOVED it! If you don’t know about Rockets of Awesome, here’s the short of it.  It’s a seasonal subscription box, where you don’t have to pay unless you keep an item. Four times a year you get eight items in a box after completing your child’s style file, and the best part: they let you preview your box and remove any items you don’t like before it ships! They give you the option to select replacement items yourself or to let them choose. Most items retail between $24–$35, and if you keep the entire box, it is only $150, about a 20% savings. You also have the option to purchase anything else from the website you didn’t receive but really wanted, and they always offer a 20% discount off four items or more! There are also special seasonal items, like backpacks or bathing suits and goggles.  

Vineyard Vines

Vineyard Vines is a classic in our house. The Performance Breaks shorts and pants are our favorites.  My son is only three, so he is still very much a mess at school.  These dry quickly, wash wells, and are soft enough there is no fight. 

The Saltwater Knit Jetty Short has a nice shape, so it can appear neater than a traditional mesh short.  I love pairing it with the Edgartown Polo and Saltwater ¼ zip for a super cozy, but not sloppy, play outfit!  They also have a great assortment of button-downs, and come holiday concert time, the cutest ties and bowties!

J. Crew

If your kid is a little trendier, J.Crew has been really hitting the nail on the head for boys! They have the coolest cargo sweatpants, available in three colors, that look great with literally everything. My top three choices are Canterbury Rugby x crewcuts shirt, classic cable-knit rollneck sweater, or colorblock Henley shirt.  The best part about J.Crew – you can always find a sale!

Hanna Andersson

We love Hanna Andersson for my daughter, but I have recently found success in their boys’ section too!  They have a great selection of pants with an elastic waistband, but that are not sweat pants! They come in slim and relaxed fit, so they work with all body types. 

If your kid is a lover of graphic tee’s, then this is also the place to set your browser to!  The Hotscotch Henley comes in four prints and is made of their classic super soft material. Nothing beats how their cotton washes and wears either! They also run promos a ton, so definitely wait for a sale!




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