Life Goals & Loafers: A Love Story

For some reason, when I first moved to New York City after college, I made a peculiar promise to myself: That when I finally became a published writer, I would use my first official paycheck as an author to buy something I then deemed the ultimate symbol of adulting — a pair of Gucci loafers. Almost 20 years later, I find a few things about this dream I longed so desperately to fulfill very amusing.
One: This was the ‘90s, when my friends and I were almost exclusively wearing combat boots, leather chokers, vintage biker jackets, and penciled brows tweezed so aggressively it hurt to actually look at them (and no, they didn’t completely grow back). At this time in my life, the only person I knew who wore Gucci loafers was a humorless, 60-plus-year-old editor employed by the magazine I’d recently begun working at as an assistant editor. This was a woman who had worn the same hairstyle for decades (a bob), and, I’m pretty sure, was the original inspiration for the term “side-eye,” for the unapologetic way she leered at people as she passed them in the hallway.
Or maybe just the way she leered at me in the hallways.
She was not a nice woman. But she was talented, and for some reason, her daily uniform of baggy belted trousers, cropped Chanel jackets, and lug-soled Gucci loafers really appealed to me as a twentysomething wannabe writer. Go figure. Two: Gucci loafers in 1998 cost $325. I know this because I saved the receipt from the Gucci boutique on 5th Avenue after I purchased them on May 26 of that year. Let me be very frank — $325 was, at that time, an obscene amount of money. And, you know what? It still is. Plenty of women would openly balk at spending that kind of money on a single pair of shoes, despite the fact that we live in an age when the latest Instagram-trending shoes and handbags can soar into the quadruple digits.
So, yeah, $325 was an obscene amount of money, especially when you’re paying double that for rent, as I was at the time for a very tiny apartment with a roommate. Add to this, the going rate for never-been-published authors was about, say, mmmm...ZERO DOLLARS. Maybe 10 cents a word if you were lucky. Very lucky.
Which, it turned out—with a lot of persistence—I was. Because after 100 or so failed pitches bulging out of a Rejections folder, I scored my first official paid assignment in an L.A.-based pop culture magazine called Detour (may it rest in peace). To my surprise, still, they paid me an unthinkable $800 for that first story — a cash windfall! — a piece that in cringe-inducing verbosity detailed the indie retail revolution happening on the Lower East Side at the time.
And, so, with one fell swoop of a check deposit — I was RICH.

magazine turned out to be short-lived (perhaps because it paid its writers so lavishly?), but that seminal life goal and subsequent “grown-up” purchase has always stuck out in my brain. The loafers weren’t just a pair of shoes to me. They were evidence of the person I always believed I was, or was going to become, hiding out for so long in a middle-class South Shore Long Island girl who harbored a secret obsession for The Paris Review and debutante-style vintage fashion. I mean, who was I?

But even at my brokest (and let me tell you, there were some very dark and broke times) I reminded myself I couldn’t be a loser — just look at my shoes.

Well, in my mind, those shoes knew exactly who I was — someone who longed so badly to have adventures, experiences, a real life. My friend, the designer Rachel Comey, once told me that she always dreamed of simply living a life that was “interesting.” That’s all. Not to be famous or rich or whatever...just interesting. And I really understood that. I still do. Because to her, and to me, and to probably so many of you, too, “interesting” is success. And finally taking possession of that interesting life almost ensured I might eventually have something to write about that was actually worth reading.
Those loafers defined interesting to me. They weren’t sexy or pretty or a "must-have" for a twentysomething girl with mounting, ulcer-inducing credit card debt. They were just simple black loafers — unassuming and pretty unremarkable to the naked eye. But to me, they were something entirely different, as if I truly stepped into a whole new life the moment I slipped them on my feet. No dramatic reckoning. No Saturn Return or quarter-life crisis crap — just a pair of elegant black shoes adorned with tiny glinting horse-bits that actually changed me. I deeply loved those shoes, my first ever luxury purchase. And I wore them for years…and years. To death! They gave me confidence with every promotion and every new story I edited or wrote. They also gave me the courage to leave traditional publishing altogether to have my first start-up experience, despite my crippling fears of navigating the world of freelancer health insurance or convincing my parents I wouldn’t eventually become destitute. But even at my brokest (and let me tell you, there were some very dark, broke times) I reminded myself I couldn’t be a loser — just look at my shoes.
Just recently, I was contemplating making that same purchase again, a new pair of loafers, almost 20 years after my maiden voyage to the Gucci boutique. The timing just felt right. It’s no secret that loafers and the Gucci brand itself are having a moment — or more like a tectonic shift, with the house and its supernova creative director, Alessandro Michele, helping to redefine what an It thing even means to someone today. And for all my good intentions in collecting just the right cast of chic-and-sensible shoes over the years, the ultimate pair of loafers had escaped me. Some were too dowdy. Others way too feminine. I wanted something classic, but also defining of the times we live in right now. And not least of all, defining of how far I’ve come since that last purchase and that very first time I was published. And so, just a few months ago, I hopped on the subway (like I did the first time) on my way up to the 5th Avenue Gucci store to make another such investment purchase. Amid towers of green boxes, I must have tried on 12 or so pairs of loafers, navigating everything from heels, studs, and brocade to patent find out which ones were THE ones. Because, let’s face it, purchases like these don't come along so often. They take time, contemplation, editing, soul searching, and a little saving helps, too. In my humble opinion, I think every person needs that "thing" to strive for. Not in a superficial way, per se, but in a way that helps make tangible — and notable — the reward of doing the real work in your life. The work that matters to you. To finally buy your own place, to recover from a hideous breakup, to go to India alone, to survive a parent or a friend — those big life moments shape our images of ourselves as much as genetics do. We deserve to choose something special, every now and then, to help honor the new chapter of that unfolding story. Don't we? For the record, my new loafers are nothing like the first ones, though they do look like something my very chic Italian grandmother might have worn — gold foil, square block heel, double gold Gs framing each foot — comfortable, practical, but also a little bit flashy and ridiculous. And maybe that's an apt description of me these days, too. Here's to sole mates.

More from Shopping

R29 Original Series