These Boots Were Made for Learning

I bought the boots.

Yes, THOSE boots.

The ones I saw on all of the impossibly thin, impossibly elegant women I passed on my way to work every day. THE fall boots of the Upper East Side. The boots of the woman I imagined I wanted to be. Glossy, yet understated. Subtle. Nothing like the supposedly “rich” ladies out in the suburbs, covered in logos and purchased at thirty percent off at an outlet store. No, these boots were refined, the kind of boots you wore on an autumn excursion to the family lake house.

I didn’t have a family lake house. I’d grown up taking a school bus two hours each way to work at a supermarket where the women who bought those boots summered because it paid fifty cents more an hour than anything local and I needed the money to pay for Advanced Placement and SAT test fees. Even as teenaged me joked with my friends about how awful the “summer people” were, a part of me suspected that they had figured out something our parents hadn’t. Something that made them look sophisticated in a plain t-shirt and shorts in a way that no one I knew ever did. Of course the quality and cost of the fabrics played a role, but I was certain that there was more to it, something I couldn’t quite put my finger on but knew I wanted for myself.

From that first supermarket summer forward, I couldn’t stop looking for it - the shirt, the dress, the bag, the shoes that would catapult me from a boring-looking, frayed-at-the-edges nerd to someone who looked the way these other people did, these wealthy people who confidently glided through life in a plain white t-shirt. I chased the high of a good buy all through college and law school, diligently studying fashion blogs and episodes of TLC’s “What Not to Wear” to figure out how to look like the person I thought I needed to be. Confident, polished, universally admired. With the right look, I was sure, I could banish the chubby, strident person with bad skin and frizzy hair from my mirror. The girl whose braces hadn’t quite finished the job, whose look never quite came together no matter how many hair products and bags and shoes she bought.

Over time, I got better at the appearance game. I dressed according to the gospel of Stacey and Clinton. Invest in your hair, your bag, your shoes. With a great haircut and the right accessories, I was that much closer to leaving my “before” self behind and becoming a full-time “after” photo. Being an “after” is expensive though, and I struggled to balance the reality of my working class student budget against the promise of the next “it” bag or shoe, the ever-increasing prices of my hip hair stylist on Newbury Street. I worked extra shifts, extra jobs, because I was certain it would be worth it, because the next purchase would bring me one step closer to feeling worthy. I’d graduate from law school and stroll on over to easy street, where I’d find plenty of funds to facilitate the transformation I was certain I needed to be happy.

Then, I graduated into the Bear Stearns/Lehman Brothers collapse and subsequent recession. I was one of the lucky ones - I had a job, a decently paid job, even as the legal industry sharply contracted. I wasn’t quite making “after photo” money, but with some strategic thrifting and use of a family member’s discount at the high-end retailer she worked for, I was on my way. Even so, so many of the pieces tI was sure I needed were financially out of reach. I constantly pursued opportunities to increase my earnings (quality of life and work environment be damned).

Which brings me back to the boots. The handcrafted, high-end leather. The discreet logo that only those “in the know” would recognize - proof to the in-crowd that I was successful, polished, worthy. After a few career moves, some raises and bonuses, I was finally making the kind of money I needed to justify purchasing the boots. (Sure, I was also working fifty to sixty hours a week and commuting for four hours every day, and I never took a vacation, and I literally flinched every time I got a notification on my work phone, but the money... surely the money was worth it?) I knew the price of the boots was outrageous - the kind of number I would certainly lie to my mother about - but finally, finally it was an amount I could afford to spend. So I did.

Trying the boots on, I marveled at the quality of the leather, so different from any other shoes I’d ever owned. Even as I bit back echoes of working class sticker shock, I knew these boots were it. I would finally become the “after” version of myself. I would finally be refined, impressive, not weird or awkward or frizzy or nerdy. And for a season, I was mostly right. That fall, I dressed to match my boots. New clothes, new bag, new hair straightening tools and serums. Some days, I almost felt like I was passing for the “after photo” I wanted to be.

And yet.

Boots don’t make twenty hours a week of commuting bearable, especially on top of fifty and sixty hour work weeks. Boots don’t give you time for your friends or family. No one cares what boots you’re wearing when you miss your goddaughter’s first birthday.

Ever since that first summer working for the “summer people,” I’d believed that I could shed my weird, awkward, acquired-taste self like an ill-fitting skin. With the right profession, the right money, the right wardrobe, I could transcend my bookish, disorganized self. The boots should have sealed my ascendency. For a brief season, it almost felt like they did.

But then winter came, and with it the missed dinners and parties, the Christmas Eve spent at the office instead of with my new husband. And then I found myself noticing THE coat. Different from mine, far more expensive and obviously better (even though mine was ferociously warm and waterproof). Surely the coat would make things better, would lessen the sting of the “I miss yous” and “where are yous” and “you’re canceling again?!”

One day, while daydreaming about the coat, I happened to be wearing the boots. They were so comfortable that I wore them constantly, and it showed. Creased, worn-in leather. Wear patterns in the soles. Still lovely, still a masterwork of craftsmanship, but also, by then, just boots. And in a flash, I saw it - this would be the trajectory of the coat. And the bag that would no doubt follow. And probably the necklace, the house, the car, the summer house. The objects I worked so hard - too hard - to buy were never going to make me less weird, less awkward, less interested in actual-play Dungeons & Dragons podcasts and graphic novels and bad science fiction shows and obscure trivia. Objects weren’t going to change how my family and friends felt about me. At best, I’d acquire enough objects to impress people I barely knew in the kinds of places I didn’t care about. Money and prestige weren’t going to fix how I felt about myself.

A month later, I had a therapist. Three months later I had a new (much lower stress, much lower paid) job. Eight years later, I have an entirely different life, one where my job and my paycheck could not possibly have less to do with my self-image and sense of self-worth.

But I still have the boots (I wasn’t kidding about the craftsmanship!).