Ericka Henriquez

On the third Sunday in May, Old Campus will be filled with purgatorial undergraduates, straddling the line between Yale and the rest of the world. Their families will gather beneath the canopy of blossoming oak, elm, and maple trees.

There will be the shrieks of parents wielding, indiscriminately, iPhones and telephoto lenses, the fluting of “Bright College Years” — and, most importantly, an endless parade of hats that would make even the women of the Royal Ascot blush.

But this isn’t Commencement — not yet. This is “Class Day,” Yale’s unofficially official excuse for every senior to crown themselves with laurels, chicken buckets, traffic cones, plush hippos, a Harkness Tower or two and at least three actual loaves of bread.

For decades, fresh-faced graduates have been gifted “Oh, the Places You’ll Go!,” Dr. Seuss’s anodyne balm for the quarter-life crisis — “Kid, you’ll move mountains!” it coos, somewhere between a self-help pep talk and the world’s longest Hallmark card. 

Yet at a time when academic freedom is under siege — from congressional hearings targeting university leaders to resignations over campus speech — Yale offers a counterpoint. The book of the hour is not a tale of wide-eyed wanderers in yellow pajamas but the far more subversive “500 Hats of Bartholomew Cubbins.”

Why? Because, dear graduates, life is not one long escalator into the clouds. It is, more often, a farce in which you try your best to do the right thing — take off your hat to the king — only to find another, and another, and another hat sprouting in its place. If “Oh, the Places You’ll Go!” is the gospel of self-actualization, “500 Hats” is the chronicle of what actually happens when you try to play by the rules. And for Yale seniors, about to plunge into a world of employment contracts, rent checks, and group insurance policies, it rings truer than any mountain-moving rhyme.

But what, after all, is Yale’s Class Day if not an entire campus-wide reenactment of Bartholomew’s dilemma? Forget the somber solemnity of Commencement, which takes place the following day, when degrees are conferred and graduates are formally admitted to the “rights and responsibilities” of their new titles. Class Day is Yale’s pre-graduation riot. It’s held on the Sunday before Commencement, nestled between the morning’s Baccalaureate ceremony and the Monday-morning march of pomp. Since the 19th century, that afternoon has been reserved for student awards, self-deprecating skits, and — most delightfully — the donning of creative headgear.

Oh, the places you’ll go? Maybe. But first: oh, the hats you will wear.

The tradition began in the groovy 1970s, when seniors rebelled against academic order and put just about anything on their heads except a mortarboard. It was catharsis, a collective letting-off of steam, a way to memorialize “the good old days” before those days became a LinkedIn post about starting at McKinsey.

These hats, much like the ones bedeviling Bartholomew, are not mere accessories. They are acts of autobiography. You’ll spot Yale’s future hedge fund managers stalking the grass in lobster claws; the nonprofit crusaders in vintage Derby hats still wearing last night’s glitter. Some hats are in-jokes only the wearer could explain, constructed from four years of inside jokes and grudges; others, as subtle as a freight train at 6 a.m.—foam Statue of Liberties, banana costumes, a lovingly detailed model of Sterling Library that took three all-nighters and at least one student’s sanity. On Class Day, hats become spirit, satire, confession, and coping mechanisms all at once. Each is a protest sign: this is who I was at Yale; this is who I might be in the world; this is who I hope to become, if the job market stops hat-blocking me.

No one is exempt, not even the most aloof faculty. Deans and professors emerge like extras from a Wes Anderson fever dream — a jester hat from Greece one year, a summer straw bought in 1945 to celebrate the end of war another. Not just whimsy — living memory.

And let’s be honest: “Oh, the Places You’ll Go!” is a classic, beloved by grandmothers and Target aisles everywhere. But its relentless optimism, however well-intentioned, often feels like magical thinking. Sure, you’ll “move mountains”—but which ones, and at what cost? In a year defined by crises from climate to campus protest, Seuss’s airy, rhyming confidence can sound a bit like telling someone stuck in Bass Library at 2 a.m. to just believe in themselves. Sometimes, you need more than hope. Sometimes, you need a hat.

So enter Bartholomew Cubbins: a medieval peasant, unremarkable except for one thing—every time he removes his hat, another appears. No matter how many times he bows to the king—through archers, magicians, and even the executioner—the hats keep coming, getting more elaborate every time. By the 500th, it’s so magnificent that even the king is forced to bow. This is the real graduation lesson: you can do everything right, follow every rule, and still find yourself drowning in unexpected hats. The world, like the Kingdom of Didd, demands gestures of submission, of fitting in, but often rewards only the accidental, the absurd, the original. Yale’s Class Day, with its silly, self-referential hat parade, understands this in its bones.

Consider the Yale journey: you arrive with a single, serviceable hat — the “smart one,” the “debater,” the “kid who built a nonprofit in their garage.” By midterms, you’ve acquired three more hats: “coffee addict,” “unpaid research assistant,” “third wheel in a suite of four.” By sophomore year’s end, you’re juggling “a cappella leader,” “FOMO sufferer,” “cryptic registrar email recipient,” and “midday napper.” By senior spring, the hats are nesting: “professional cover-letter writer,” “first-gen trailblazer,” “unpaid internship survivor,” “friend who remembers allergies,” “person who asked a Nobel Laureate a dumb question,” “person who will never live down asking a Nobel Laureate a dumb question.” On Class Day, you wear them all at once, and — miraculously — the world applauds.

Even the Class Day speakers get in on the act. Hillary Clinton once brandished a Russian fur hat and, in a moment of perfectly Seussian absurdity, quipped, “If you can’t beat ’em, join ’em.” (Her other hat, presumably: “Global Democratic Stateswoman Who Still Thinks About 2016.”) This year, Jacinda Ardern will bring her own hats — Prime Minister, Pandemic Hero, Empathy Maven, and, surely, the “Yale Honorary Kiwi Hat,” awarded to dignitaries who can explain New Zealand’s political system in under two minutes.

But the true stars are always the students. There are hats that look like bees, hats with cameras, hats in tribute to residential colleges, hats that light up, hats that play music, hats that simply announce, “I survived.” The more outlandish, the better. It’s Yale’s final group project, one last piece of performance art before scattering to the world. This isn’t mere silliness — it’s ritual. It’s how you shed the pressure of achievement and embrace the pageantry of being exactly who you are (and all the selves you tried on, and the ones you’ll grow into next).

So, to the graduates: accept your hats, every one of them. Wear them with the wild confidence born of four years of success, failure, reinvention, and 2 a.m. pizza. Wear them in job interviews, on first dates, when the world is impossibly cruel, and especially when it’s impossibly dull. Life will hand you new hats whether you want them or not — let your time at Yale teach you to wear them lightly, tip them to the kings, and keep searching for the one that feels most like you. The rest is just headgear.

And for those parents still clutching “Oh, the Places You’ll Go!”: may I humbly recommend a new gift for your next graduate? It’s the story of a boy, 500 hats, and the delightfully unpredictable future that lies ahead. First comes Class Day, then comes Commencement — and somewhere in between, the real world begins. Welcome to it, Class of 2025. May your hats never stop surprising you.