The weekend before school started was all about getting the kids ready for back to school. We participated in an annual right of passage, one I always looked forward to as a little girl, back to school clothes shopping! In our family this event is preceded by the semi-annual kid’s closet and dresser organizing extravaganza. I thought I’d share some observations about what worked, in hopes it can streamline your school clothes shopping spree.

Observation number one: boys don’t like to try on clothes. So this year, we did some decision making before trying on clothes. Collin has inherited hand-me downs from a few different sources. This, coupled with playing on multiple sports teams and going to sports camps meant he had an over abundance of t-shirts. (I’m talking loads and loads of t-shirts.) The first thing we did was sort all the clothes…those in his closet, those in the newly acquired hand-me down bags and those in the out of season / too big bins in his room. We grouped like items together: T-shirts with t-shirts; jeans with jeans; shorts with shorts; etc. Then, instead of making him try on everything…we first decided what he liked and what he would actually wear. The questioning went like this. Me: “Do you like it or dislike it?” Collin: “Uh, I don’t know. I guess I like it.” (Yes, that was the answer for the first ten or twenty shirts.

Observation number two: this line of questioning isn’t working. It’s time for a new approach.) Me: “Do you like it or love it?” Then we were onto something. Somehow, it felt better to him to identify just the shirts he loved instead of saying he didn’t like something. So, the shirts he “just liked” went into the giveaway pile; the items he loved went into a second tier of decision making. In this second round of decision-making, we decided if an item was school-worthy or weekend-worthy. T-shirts and sports shorts, for example, went into the weekend pile; collared shirts went into the school pile. Once we had items grouped into the keep for school pile, Collin tried things on to see what fit. Items that fit were keepers; items that didn’t went into the giveaway pile. After doing this sorting and trying on, the school shirt pile was very empty…not too many school-appropriate shirts in our midst, so we added collared shirts to the shopping list. He needed, at a minimum, five collared shirts, one for each day of the week.

Now…while we’re on the topic of quantity of shirts, I have to ask you to ask yourself, what is your comfort zone? How many unique shirts (or sweaters, pants, skirts, etc.) is the right amount for your kids to have to wear to school? Is one different shirt a day for a single week enough? Or is two weeks enough? Three? Four? There’s no right answer here…only comfort zones. The key is to identify your comfort zone, and then, add that quantity of items to your shopping list. If you go through this process item by item, at the end of the closet organizing session you’ll have a terrific shopping list that you can take with you to the store. The four of us went through this process for Collin, and then, Jay and Collin hit the stores. (Kailea and I had created her list the day before, and went on our own shopping expedition.) The boys were much faster shoppers than the girls, which leads me to…

…Observation number three: boys don’t like to shop; girls do. But with a shopping list in hand, the process was simple and fun for everyone. Each team of shoppers knew exactly what they needed, and that took a lot of the stress out of school shopping (even for the boys.) This approach also kept us from buying loads of items we didn’t need (and would just have to spend time dealing with later.) So that’s how we did it.

How about you? How do you approach back to school shopping? I’d love to know your techniques and strategies. What works for you and your family? Do you do one big shopping trip at the start of the year…or do you buy a little bit at a time here and there? Please share. I’d love to hear from you!

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Aby Garvey is a creative organizing expert and simplify 101’s founder. She has created 14 online organizing classes, which she has been teaching since 2007, helping thousands of people around the world get organized. Aby loves to help people create positive change in their lives through her online classes and organizing eBooks.

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