What Thing Did You Think You’d Love Forever?

I like to think of myself as a loyal person — as stalwart in my love of cashmere and Mindy Kaling and Brussels sprouts as I am in my devotion to my (real) friends. Given that, I am sort of mortified to admit this most recent development. After years of unwavering commitment, my riding boots and I have decided to separate. The seven-year itch is a cliché, but it fits the narrative.

I got my first pair of tall boots when I was 15. While I assume I had experienced some kind of leather footwear before them, these shoes were a particular revelation. Like statement jewelry and leopard print and the absurd patent leather motorcycle jacket I wear just about once a year, they could transform even the most mundane separates into an “outfit.” They made leggings look polished and oxford shirts look intentional. They made me look more like Charlotte Casiraghi — an enduring fantasy. Each time I yanked them on in the morning or before I left for dinner, I rewrote myself a little bit. I stood taller and strode with purpose. I imagined I had a prize-winning horse named Bernie. It was all very romantic.

But then, about a year ago, I moved to England for five months. It did not take me long to acclimate. During the time I spent on Maple Street and in the depths of Kensington, I learned to like milky tea and crumbly biscuits and the fundamental English disdain for physical exertion. I learned to imitate the way my new friends got dressed each morning: flouncy printed mini-skirt, slouchy sweatshirt, combat boots, and a swipe of the sexiest lipstick you ever laid eyes on. It was easy. In fact, I was so enamored of the aesthetic that I sort of forgot about the (Loeffler Randall, jet black, would-be perfect) riding boots. Here was the cultural immersion I had been promised, and I loved it.

I guess I expected there would be some grand reconciliation after I ended things in London. I would return to New York and fall for the boots all over again. It seemed only fair. I have, after all, spent the past five years in pursuit of the timeless wardrobe. The reason I buy “the classics” is that they’re never supposed to go out of style. Leather accents are infinite. Fisherman sweaters are eternal. Audrey Hepburn wore riding boots. And yet in October — as the season for thick socks and obscured ankles rolled around, the truth was undeniable: I hated them. They seemed tired and juvenile. They seemed…suburban. There is no worse crime.

“Everything has an expiration date,” my mother maintained in the face of my despair.

“Like Greek yogurt. Or Advil.”

“So untrue,” I countered. “Some relationships last forever.”

She agreed. But then she stated the obvious: “You are not in a relationship with your boots.”

I swear I know this. The boots and the sweaters and that inky pair of jeans I wore on every single first date last year are not people. They do not protest neglect. You cannot hurt their feelings. And yet whatever it is between us seems real. The clothing I like best has taken me places and seen great things and witnessed several terrible dinners. Maybe that explains why I mourned the riding boots — just a little bit. Maybe that explains why I’ve held on to them. You know how it is with old flames.

What was the thing you thought you’d love forever?

Image shot by Mario Testino for Stuart Weitzman SS13