In the late 19th century, it became common for English sportsmen to travel to Norway with their wooden fly rods. The waters teemed with salmon, and the region was scenic. After a long day on the river, they would return to their lodgings and trade their wading boots for TESERS — moccasin-like leather slip-ons worn traditionally by Norwegian farmers. At some point, the Brits decided that the TESERS were not only comfy enough for post-catch relaxation, but chic enough to sport on holiday in the French Riviera. Fashion magazines and shoemakers took notice, and eventually the style trickled across the Atlantic. In 1936, G.H. Bass & Company debuted their first casual “loafer.”

As far as shoes go, the loafer is as simple as it gets. Its body is essentially three pieces: two sides and a connecting midsole stitched together with black thread, sitting atop an unembellished quarter-inch heel. The midsole is the shoe’s most iconic feature. On it is a single strip of leather laid flat across the upper with a horizontal quarter-moon-shaped opening cut out of its center. It hugs the shoe’s body like a too-short blanket or an ill-conceived tube top. It looks like the eye mask Robin would wear if he were both drowsy and a Cyclops. It’s the bottom half of a face with a cleft chin and a mouth slightly agape, as if it had reached a particularly troubling scene in an episode of Black Mirror. The shoe’s wearers developed a propensity for shoving small currency into this opening — hence the moniker “penny loafer.”

The insole, a sweat-proof, semi-perforated strip of leather glued snugly into the heel, announces itself boldly:



I’ve never been able to keep a journal. My Aunt Navis bought me a diary that I wrote in for a few months when I was eight, but its entries are few, and the lion’s share are just idealized pencil drawings of my future self (a handsome, muscly quarterback for the Philadelphia Eagles). The most journal-like thing I possess, the thing that best conveys who I was and what I cared about, is my bookmarks folder on Google Chrome. I sourced most of its contents during my final two years of high school, a pivotal time in my life; a time when I was chiefly concerned with “the 2012–2013 NBA Regular Season Conference Standings,” “‘Enter the New Negro’ by Alain Locke — PDF,” and “The 21 Hottest Models Under 21”.

I was also ensconced in the world of traditional menswear or “trad” — the puzzlingly lively internet subculture² populated by old Yankees, sartorial nerds, Japanese Americana fetishists and me. I bookmarked blogs like “Ivy Style,” “The Sartorialist” and the short-lived, but fondly remembered Brooks Brothers vehicle “Of Rogues and Gentleman.” I started wearing cardigans and boat shoes. I even applied to Princeton.

By 2010, I had spent five years at Hamden Hall Country Day School, a small, private high school nestled in an affluent corner of a New Haven suburb. Though I had been going to school there for some time and was well acclimated (played sports, did debate, went to parties), I never felt like most kids there; mainly because I wasn’t. I was one of only four black students³ in my 53-person class. After school, they’d flock back to big homes in Woodbridge or Orange; I had my little house on the “bad” side of Hamden. Come sophomore spring, they’d show up to school in new BMW’s; I lept out of my mom’s ’01 Saab wagon, hoping she’d exit the parking lot before too many people noticed the loud screech it made. At the end of the year, they invited people over to swim in their heated pool; I wasn’t always sure if our house would have heat. I went there, but I wasn’t from there. I was in, not of.

Trad was my rebuttal. I may not have a BMW or a pool, but I can look like I do! This, of course, was not what I told myself, nor something I would ever have admitted to at the time, but it undoubtedly was the logic underpinning my unexpected, sartorial obsession. Suddenly, those Oxford shirts my mom had bought for me “to grow into” were appealing. Suddenly, I actually wanted to go shopping with her, tagging along on trips to Goodwill, snagging second-hand Brooks Brothers chinos and used sport coats.4 Suddenly, I wanted Weejuns!

They were brought to my attention by the aforementioned Ivy Style, a blog whose editor’s twitter bio reads, “jazz, golf and tennis, gin & tonic, Ivy League clothes, la dolce vita and a sense of irony.” The post was a scan of a G.H. Bass & Co. magazine advertisement from the 50s that featured a pair of Weejun-clad feet dangling from a stool next to small stack of books. It read:




by Bass5

I wasn’t entirely sure what the classics were, but I knew I needed those shoes. I didn’t have the $110.00 to shell out for new ones, and, broke snob that I was, I couldn’t bear to settle for a cheaper, virtually identical off-brand pair. For about a year, I pined in irresolvable angst, until, by the grace of God and Hamden’s Goodwill, they were delivered to me.

My mom had discovered them. In my sudden turn toward prepdom, she had finally found an interest of mine from which we could both derive nearly comparable enjoyment. My forays in lacrosse and football were too rough and anxiety-inducing for her to watch in complete ease. Hip-hop simply wasn’t her cup of tea. But trad! Trad was the point where her instinctual, industrious, put-your-best-foot-forward, immigrant respectability politics meshed seamlessly with my manically obsessive bend and juvenile desire to look richer than I was. So she enabled me. After hauling home a couple, not-quite-Weejuns from Goodwill that I couldn’t bring myself to wear, she struck gold on her third attempt. They looked nearly new. With the exception of small squeaking noise that the left heel made mid-stride, there was virtually no indications of wear. I, in turn, wore them every chance I got: If I had a debate tournament, if I had to “dress-up” for a game day,6 at any and all family gatherings. Frankly, if I hadn’t been worried that they would draw more stares than compliments, I probably would have worn them every day to school.

By the spring of my senior year, it felt like mission complete. I was captain of the lacrosse team, I looked great — wool cardigans, pink oxford shirts, blue cable-knit sweaters, boat shoes — and I had gotten into Yale. The prep oasis of the Ivy League awaited.

At Hamden Hall, the social strata I’d aspired to was one bedecked in Vineyard Vines fleeces and L.L. Bean duck boots. Through trad, I’d not only achieved this look but, in my eyes, had captured its purest, most authentic form.7 In college, that form had taken on a shape I hadn’t expected. I arrived at Yale in the fall of 2013 to find that collegiate “cool” didn’t necessarily look like an Ivy Style post. “Cool” was the basketball player from Portland, Oregon in a kitschy, vintage Jimmy Buffet t-shirt, rolled up chinos and tiger print socks. “Cool” was the kid from New York City wearing black, worn out, vaguely orthopedic-looking Clark Wallabees like the ones my dad owned and distressed raw denim jeans with janitor keys hanging off of the side. “Cool” was the girl from Danbury with shaved head and the septum piercing. Where Hamden Hall had been a local grocer with a small, regionally specific selection, college was a WAREHOUSE SUPER STORE filled with more brands, flavors, varieties, species of “Cool” than I knew existed.

I also discovered that in a social ecosystem larger and exponentially more diverse than the one I inhabited at Hamden Hall, many of those who dressed “preppy” were not people I particularly identified with. Freed from the constraints of a 53-person class and the social imperative to “fit in,” I began to see that, unlike Matt from Our-Family’s-Lived-Here-For-Centuries, Massachusetts, I could not afford to pay for the laundry service, and, despite the oars on my baseball cap, I did not “row for a club.” Aesthetically, I was presenting as someone I wasn’t. And with this realization came an increased discomfort in my trad garb. Each month, it seemed, brought the retirement of another preppy piece from my wardrobe. No more boat shoes. No more vests. No more crew hats. No more Weejuns.

Nice leather shoes age like dogs. Each time you see them they don’t really look any different from the last. Around year five, though, they invariably and suddenly start to show their wear. My Weejuns are coming up on year six. The black stitching on the midsole have begun to come undone, first distressing to a sandy brown color before, eventually, fraying to strands. About an inch of each sole has been ground away, revealing the horseshoe-shaped constellation of nails that bind the heel to the body and reducing the white-threaded stitching of the welt to what now look like little dots of putty encircling the toe. The burgundy leather is cracked, scratched and wrinkled. The area towards the front of the shoe, below the midsole strap, is striped with creases, and the rivet-like stitching that connects the three pieces of the shoe at the toe has clouds of crow’s feet that trail like rust from a door hinge.

Lately, I’ve been wearing them again. My senior society requires that we dress in “formal attire” for our weekly dinner. Typically, I pair my them with a navy blue blazer, blue Oxford shirt, rep tie and pressed grey chinos — my old trad staples. The prospect of wearing this uniform, however, is no longer something I look forward to as eagerly as I did in high school. In fact, most weeks it feels like an inconsequential, if mildly inconvenient, chore. I still pay attention to the way I dress, but I don’t as often go elsewhere for cues. I prefer fishing in my own waters now.


1. In case you missed it, this was some G.H. Bass & Co. ad executive’s cute, phonetic play on “Norwegian,” the shoe’s country of origin. We’ve all seen Mad Men.

2. Well, aren’t they all?

3.  Two of them were twins.

4. Goodwills are different in Connecticut.

5. I’m not positive that this was the post that made me a Weejun convert, but it’s soaked with the New England prep school, prestige-evincing overtones that I would have eaten up at that time. For what it’s worth, a post about Miles Davis walking out of the Andover Shop at Harvard with a pair of Weejuns and “never looking back” stands out in my mind as well.

6. Wearing more formal clothing on the day of an athletic sporting event was common practice at Hamden Hall and many prep schools in the area — “look good, feel good, play good!” Go Hornets!

7. I.e., approximated it via the discarded clothing of old white men.