Back to School Clothes Shopping For Preppy, Nostalgic Grown Ups

There’s no back to school police who says I can’t wear knee socks and a backpack even though I have no textbooks right?
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Alyssa Garrison
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There’s no back to school police who says I can’t wear knee socks and a backpack even though I have no textbooks right?

Back to school shopping is a family tradition I hold near and dear to my heart. My family really liked to make a big deal of going out and getting special new outfits for the school year every August, and as silly as it sounds, some of my favourite memories with my parents are from those big shopping trips.

We’d head to the main shopping street in downtown Vancouver and make a day of it, picking up lunch at a nice restaurant and trying on all sorts of outrageous outfits. 

Me on my way to the first day of kindergarden. Tiny pink satin backpack not shown. 

Me on my way to the first day of kindergarden. Tiny pink satin backpack not shown. 

I went through a whole bunch of style phases as the years went by, choosing everything from pink Spandex track suits to pleated miniskirts with matching socks for the first day of school, but every outfit had a hint of undeniable prep. When I moved to Toronto for university, the family-funded back to school shopping came to an abrupt stop (as it should have), but I still always found a way to buy myself a special new pair of shoes or a backpack each September. 

But then, graduation happened. This September marks my second year free of schooling, and though I don’t miss rushing to classes and being bored out of my mind half of the day, I do miss my back to school shopping and outfit planning. I suppose that I can still do those things though, can’t I? I mean there’s no back to school police who says I can’t wear knee socks and a backpack even though I have no textbooks right? After all, Candy Pratts Price did say, “September is the January of fashion.” What better time is there to mix up your look and reinvent yourself? 

Here are some of my favourite back-to-school inspired looks, and a few items I’d be buying anyway.

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I've been watching a lot of "Gossip Girl" reruns, and like Rachel, I'm 100% channeling Blair Waldorf with this ensemble. I think my glittery Ban.do headband and matching glittery Golden Ponies shoes really pull the whole thing together, don't you? 

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White dresses are so not just a summer thing. I love pairing this cute lace Betina Lou number with cardigans and sneakers for that off-duty cheerleader vibe. 

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I'm firmly on team "never too old for backpacks," and this hologram Golden Ponies bag is pretty much my new favourite thing (and it's vegan leather!)  

What are your favourite back to school looks?