Remember Your Favorite First Day of School Outfit?

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A tragic story of how I fell out of love with my favorite outfit…yup, I would like to reserve my seat in the Suburban on the way to 4th grade to hear about this one please. 

My first day of 4th grade had arrived. I wouldn’t be the new kid like I was last year. I knew the faces and names I would be seeing again after summer break, but I also knew what brands I would need to be wearing on the first day of school to land myself in the ‘cool’ category (Honestly, I was perfectly content with ‘Acceptable’). For my elementary school you had 3 options: American Eagle, Hollister, or Abercrombie & Fitch. 

The town I grew up in wasn’t big enough for a mall, so every August my mom would take my sister and I to our neighboring city for a back-to-school shopping trip. For me, this was like one of the top 5 greatest days of the year – New clothes (within a budget), all the brand options that a 10 year old kid could want in one place, and freedom to choose my own style? Yup, I would like to reserve my seat in the Suburban for that one please. 

For my sister, it might have ranked in the top 5 worst days of the year. She was not too keen on the idea of keeping up with what was cool at school and especially so when it came to clothing. Because of this, setting aside an entire afternoon for trying on clothes seemed like a huge waste of time that could have been better spent reading, watching NCIS, or doing literally anything else. My mom basically operated as Sissie’s personal StitchFix stylist for the better part of her growing up years and by the end of high school, they had a pretty good system down so that she no longer had to accompany us to the seventh layer of Hell – otherwise known as the shopping mall. 

Even though I was 10, I had a clear idea of what brands I aligned with stylistically and which ones I did not. Hollister stores were a little too much tiki-hut / young Tommy Bahama for me and Abercrombie & Fitch gave me sensory confusion with the dim lighting, giant shirtless abs, and the excess of cologne hanging in the air like a fog machine at a Van Halen concert.  

That left me with American Eagle…After enjoying my time exploring everything that they had to offer for the Fall Season of 2007, I settled on my first day of school outfit. A pair of blue, green, and white plaid shorts accompanied by a matching green t-shirt emblazoned with a large unsightly logo… but I was 10 and the brand was 90% of it (If we’re honest, I don’t know that too much changes once we graduate to grown-up fashion). 

On Monday morning, I donned my new favorite outfit complete with all-white leather Puma’s that pulled out the white accents in my plaid shorts. I couldn’t have felt more ready for my first day and it did everything I needed it to do – Show that I tried without calling undue attention to myself. 

I wore that exact same outfit once a week for the first 3 months of school. It was what I would wear on the days when I needed a little something extra or on a Friday to finish off the week on a high note. 

But then it wore off… I became bored with my favorite outfit. It was a sad day when my ‘power-suit’ lost its luster. I had worn it so often with so little variation that it no longer made me feel the way it once had and I almost despised it as a reminder of my lack of creativity. 

Thus began my slow shift away from buying outfits and towards buying pieces. Buying an outfit is like putting a lock and chain around pieces of clothing so that they can only ever work with those pre-determined partners. Buying pieces is how you would approach inviting a new friend to an established social-circle – Will it play well with the others? Does it fit within the boundaries while breathing new life and fresh perspective into it?

Buying pieces is so much more interesting than buying outfits and because you let them interact with the rest of your wardrobe, you are far less likely to become bored with them because there is always another dance partner to introduce them to. 

We can learn a lot from how our 10 year-old selves approached back-to-school shopping. First, clothes should be something that make us feel like the best version of ourself – ready to take on the world (or playground). Second, figuring out which brands feel like ‘you’ can make your shopping experiences much more successful and enjoyable. Lastly, when we don’t limit ourselves by creating outfits and instead create a wardrobe, we can enjoy our favorite pieces for years instead of seasons. 

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