Back to School Shopping and Imposter Syndrome

A harrowing look at my mostly imagined childhood trauma

In my hometown, there was a second-hand children’s store called “Children’s Orchard” that my family frequented. It’s one of those stores that had a very distinct smell to it— not bad necessarily, just the dizzying combination of a million people’s different laundry detergents, disinfectant spray, and generally the smell of baby in the air. It was the kind of store that has the constant sound of squeaky hangers on a round rack being pushed and pillaged through.

A second-hand children’s store makes perfect sense. Kids are constantly growing out of clothes and toys. It’s both a benefit as a shopper and a seller when your toddler is sizing out of their little jumpers at lightening speed. But to elementary school aged me, our family went to Children’s Orchard because we didn’t have Limited Too Y2K mall money.

I grew up in a very affluent neighborhood, literally The O.C. And let me be incredibly clear: we were by no means struggling (and if we were, my parents certainly didn’t tip us off). I had it all growing up—every book and CD I could imagine, magazine subscriptions, I was in dance classes and acting classes, Santa brought an American Girl doll for Christmas, we went to Disneyland, and on vacations— it was an incredibly wonderful life.

But when you’re seven and dumb, all you know is that everyone around you has it way, way, better. In every aspect of my world, it felt like there was this massive divide, this hard to pinpoint feeling that our family was somehow different. Nothing exemplified this more clearly to me than fashion. I went to public school, and it was an endless parade of girls in outfits and brands I could never in my wildest dreams convince my mom to splurge on.

Every year, around this time, I would hear murmurings of back to school shopping.

“Have you gone back to school shopping yet?”

“Yeah it’s new, we got it back to school shopping at the mall.”

“I don’t know where it’s from, my mom got it for me when she went back to school shopping…”

The act of back to school shopping was discussed amongst peers as if it were shopping for groceries, something sort of mundane that all of us did. I would see the bags from Abercrombie Kids, Tilly’s and Nordstrom, overflowing with new fall fashions at other people’s houses. Back to school shopping in our house meant going to Staples and picking out a new notebook or binder. Maybe a Spacemaker if we were feeling wild.

I would gently ask my mom about back to school shopping, hoping and dreaming she’d be as enthusiastic about the idea of a mother-daughter shopping spree as I was, even though her least favorite place in the world was the mall and she told us that constantly.

“Do you need something for school that you don’t have?” she’d ask me.

Yes. I needed to be seen as cool what wasn’t she getting? I wanted to waltz in on the first day nearly unrecognizable, with an entirely new wardrobe, an entirely new personality!

I’d mumble something about not having good tops or comfy shorts and be met with,

“Well why don’t we go through your drawers and see if there’s anything you can bring to Children’s Orchard.”

Unbelievable. How could she do this to me? Not only was I not getting a shopping spree, I had to clean out my drawers? A chore!? And let’s say I was able to sell things to the woman at Children’s Orchard for Orchard Bucks or whatever, what were the odds that the cool new Roxy top I wanted or Limited Too henley was going to be on the racks in the “big kids” section?

I’d inevitably go through all my clothes and bring a pile in to the small room at the back of Children’s Orchard. I’d take my measly earnings and methodically go through the racks. Back then, I was annoyed beyond belief, but looking back, I think it was actually the beginning of developing real personal style.

I’ve never been inherently cool.

So much of being “cool” when you’re younger, and let’s face it, even when you’re older, is having money. Are you wearing the right things, are you going to the right places, are you eating at the right restaurants, living in the right neighborhood? It’s expensive to be cool.

As an adult, I share proudly that most everything I buy is second-hand and feel absolutely no shame whatsoever. In fact, I even feel a sense of smugness about it sometimes.

“Anyone can go online and order something off of Zara or Madewell,” I tell myself, “but I am curating a chicer and more unique wardrobe of higher quality pieces, while saving the planet and saving money!”

This is of course, a horrible line of thinking because it is still so deeply rooted in caring what people think of me. I’m also patting myself on the back and tossing in a little dash of covert narcissism I disguise as altruism like some sort of congressmen.

Regardless, the pendulum has swung in recent years and thrifting has become “cool”. TikTok has even seen recent trends of “de-influencing” and “underconsumption core” videos that promote incredibly normal spending habits and second-hand shopping often set to a Norah Jones song. Luckily I have been training for this since I was fighting for my life in the racks at Children’s Orchard.

When I sit with these thoughts, I desperately want to be someone who doesn’t care what people think, who doesn’t need a new outfit for every function I attend, who isn’t so enchanted by brands or luxury goods. That feels like true enlightenment. As I get older, I find those kinds of people to be way cooler anyhow, comfortable in their skin, assured of themselves. And yet there is still this part of me, this cranky tween deep within, that longs to be seen as a cool girl.

The thought has popped into my head more recently as I begin this journey of doing content creation full time.

Internet influencers (is that word even what I want to be?) are the cool popular girls from school on steroids. I feel stirrings of those all too familiar feelings and I am THIRTY-ONE YEARS OLD. Shouldn’t I be more secure? I am more secure than that girl who’s entire life revolved around an unattainable Limited Too skirt in 2002. The girl who’s ultimate goal was to be perceived in an elusive, meaningless light that I equated with being better somehow.

It’s endless and it’s silly. There will literally always be someone prettier, smarter, younger, richer, thinner, cooler, hotter, funnier, whatever— who’s only real threat to me is that they distract me and waste my time. The hours I’ve thrown away comparing and stressing when I could have been perfecting the art of me, that’s just incredibly uncool all around.

I’m working hard right now to develop my brand, and frankly, grow a business. I’m spending a lot of time thinking about what I want to put out into the world, what I want to add to the conversations being had, and how I want to be thought of. So much of “all” “this” is turning me, Shannon, into a product. And though I’ve done an okay job so far, I think a part of me wonders deep down,

“Am I cheap goods?

I was recently consulting with someone who does PR for a living who said that there seemed to be an element of myself I was holding back. That I wasn’t letting myself fully shine. And she’s right! There is this scared little part of me that worries too much about being “cool”. Of being outed as a fraud in some way. A familiar spiral rings in my head,

“They’re going to know I don’t really go back to school shopping. That I got this shirt at Children’s Orchard and it sort of smelled weird when we brought it home…”

What I could never do when I was little, and what I am pushing myself to do now is to say in retort,

“And?”

Let the whole world know I can’t afford an Oscar de la Renta wedding dress fresh off the rack, let them know my Everlane sweater came from Poshmark. Maybe even be proud of it. What would happen if instead of tripping over myself to finish last in the imagined cool-girl Olympics, I just dropped out of the race? What if I reckoned with the deeper insecurities bubbling up of not being good enough, not being worthy, and instead of blaming any exterior thing I decide I lack, I gave myself a break.

If I could time travel to my little self, with all money in the world, I think I would still let her rummage through the bargain bins. I’d let her huff and puff in frustration and develop her scrappiness back there. It didn’t feel like it at the time, but I was discovering who I was within the racks of Children’s Orchard. The early seeds of a lifelong passion for curating a meaningful, beautiful, thoughtful life were being planted.

Twenty-ish years later, I think it’s time to outgrow my insecurities once and for all. I’m done pretending to be cool, whatever that means.

I’m ready to be defined by so much more than my clothes. I’m ready to shine.