It’s always a mad dash around here getting the boys ready to go back to school. Even though end of summer is bittersweet, it’s so heartwarming to hear Knox ask when he gets to see his “school friends” again, and to see Andrew want to be just like his big brother by having his own backpack and school supplies and this year he will be at “Knoxy’s school”!

At these ages (four and two), the boys grow through their clothes so quickly, which means the start of the school year is always time to shop for comfortable basics and some fun pieces that I know they will love wearing again and again. I was very excited to hear about Gymboree’s recently updated brand and clothing pieces that are perfect for back-to-school (more on this below!).

In addition to back-to-school shopping, there are always schedule adjustments that have to be made to get back into a groove. The summer-to-school transition is not always easy — especially at this young age where a change in daily habits (and nap time) can lead to emotions running high. I’m trying to stick to a few new habits this year that will hopefully help everyone adjust a little easier. Read on below for details about our back-to-school routine and a couple of favorite new outfits!

Early Morning Breakfast & Quality Time

Thankfully the boys (definitely Andrew) are early risers, but it’s still tricky to segway from lazy mornings lounging around in pajamas to getting dressed and out the door at a very early hour. To encourage them to be excited about the early morning structure, I try to make breakfast a fun time around our kitchen table together. I surprise them with some of their favorite early morning treats, like waffles, and make sure to leave my phone tucked away so I can be fully present as I’m getting them fed and ready for the day. This quality time in the morning makes it easier to drop them off at school and helps everyone start the day on a good note.

Nightly Outfit Line Up

I’ve found that the boys actually like to pick out their outfits the night before, and then enjoy getting to put them on the next morning. This saves all of us so much time and energy, which is much appreciated! It also eliminates the “I don’t want to wear that!” in the morning because we already all agreed on it the night before. (Last year Knox started a phase where he wouldn’t wear anything with buttons on it.  That was fun.)

As I mentioned, Gymboree recently launched a new collection of pieces that are super comfortable and also easily mixable making it fun for the boys to “dress themselves” and pick out what they want to wear. I’m obsessed with their cute little cords and flannel shirts that are perfect for the A/C classrooms. The styles are dressed up enough for the classroom, but are also comfortable for running around all day and being on the playground.

Gymboree also recently launched a fun new free app called “Made You Smile” that has adorable smile filters and stickers that the boys love playing with, as well as a built in sweepstakes that guarantees you will win a prize every time you visit one of their stores. Talk about a great incentive for getting little ones to the mall!

Prep Ahead Lunches

Making lunches in the morning is probably my least favorite school routine activity. To make it a little easier, and more fun, for myself I’ve been trying some new lunch ideas and prepping as much as I can on Sundays so that I don’t have to spend time in the morning starting from scratch. I know the boys will love that they are getting some variety instead of the usual sandwich rotation, and these new lunches are appealing to me as well, so I can pack a lunch for the office!

After School Play Dates

To help the boys meet new classmates and keep them excited about school, I try to schedule an after-school play dates once a week. It’s a great way to make sure they are getting to know everyone in their class and feeling comfortable in their new setting. It’s also nice for me to get to know new moms and to visit with the ones I already know!  Since our boys are in a neighborhood school, most the families live just a few streets away which makes it super easy to get together.

Do you have any tips for starting the school year off on a positive and productive note? I would love to hear in the comments below!

This post was brought to you in partnership with Gymboree. As always, all opinions are my own.  Thank you for supporting the brands and products we love here at HOUSE of HARPER! #MadeYouSmile