What To Wear To Middle School.

It's hard to believe that Easton (my Young Bibliomaniac) will be heading off to middle school this year. I still remember how he (and I!) cried nearly everyday for weeks when I dropped him off at Kindergarten. Oh, how the time flies.

There are so many great things about having older children. The conversations, the laughs, the free babysitting. . .  One of my favorite things lately is seeing Easton's personal style develop. He has an opinion about the color and style of his shoes + what fit his jeans are. It's made school shopping especially fun (and frustrating) this year. We've weeded through a lot of stores and have come up with our favorite back to school essentials to share with you.

Dakine Varial Backpack from Altrec $49.95 | Bold Buffalo Paid Shirt from 77 Kids $29.50 | Super Stitch T-Shirt from Johnny B. $28 | Original Fit Jeans from Gap (faded black wash) $25 | Adidas Retro Gazelle Sneakers from J.Crew $45


  1. I love the name Easton. He sounds like my third child. We both cried when he went to kindergarten. He had to go all day every other day. It was awful. Then when he went off to College he went to Florida....we live in Ohio. Then he was stationed in Hawaii with two tours over seas. He now lives across the country. When he told me he got accepted into FSU, I said, "That's not funny, go to your room." Yes, I did.
    He used to keep a chart on what he wore each day to middle school. He didn't want to repeat anything for a couple of weeks. My oh my. You wouldn't believe what he does today. Very under cover work....that's all I can say.

  2. Love his choices, especially the shoes!

    I'm still slightly in denial that these kids are going to Middle School.

  3. I LOVE all of these clothes! Just went school shopping for my Kindergartener yesterday so I too have boy clothes on my brain. I wanted to add that Zara Kids is a fabulous place to shop as well. Priced similar to GAP Kids, but with more trendy and European styles. They have amazingly cool and cheap shoes and lots of hip, but classic pieces. Thanks for sharing your finds with us! And I'm hoping that my family experiences less tears than you described when school begins!

  4. I enjoy your blog, think it's great that your son is obviously inheriting your sense of design and style. But what about thriftiness? The one outfit you showed cost $177.45, that's almost half my school clothes budget for all six of my kids this year! You guys are so crafty, you could buy a $3 shirt from Walmart and stencil cool designs on it, and spend the other $25 bucks on 2 more pairs of shoes! If you really spend this much on one school outfit, how much do you plan on spending when all 5 of your kids are school-age? I'm not criticizing, just wondering how you make it work in real life. Love the outfit, though. Our eleven year old boy is looking remarkably similar these days. Please keep up the great work!

  5. Hello Heather,

    I'm all for thriftiness too. WIth five children (4 in school) I have to be. There are certain brands I'm loyal to because of quality + fit. Gap is one of them. Every year I purchase my children's jeans on clearance in early August. A few weeks ago I snagged 8 pairs for under $100 using coupons. When purchasing items online, I always hunt down coupon codes. For items like the backpack and shoes, I try to get the best deal while still getting quality items.

    I know a $50 backpack sounds like a lot but I have every expectation that it will carry Easton through high school. (The last one we bought him he used for 6 years, K-5th grade) And don't forget, I have 2 other boys that will get use out of those items in the future. :)

  6. hey heather, another thought for being practical $-wise with school clothes and multiple kids (perhaps this is more for older school-aged kids, MS & up), and even though this won't plug the gap like the jeans in this post, giving AE a whirl may be another great idea for making your B2S budget go further. their return policy is great, regarding the quality of their products. if there's something wrong with the clothes like a strap comes off or the jeans wear through, they'll replace it with the same item or a one that looks like it/in the same price range. plus they don't have a time limit on returns like other stores (such as 90 days or something to that affect). so check with your favorite retailers and find out about their policies regarding their clothes wearing out. this is a great one that we've loved for years, especially with AE's denim. only had to lean on that policy once or twice, but they were great. talk about making your money stretch, + peace of mind that your kid looks great and you have that added "insurance" that you made a sound wardrobe investment!

  7. Let your kids pick what to buy, because you have veto power over what they pick, and if you don't approve of what they want to buy, you just don't buy it.


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