Fashion Gets Funny

A 2023 fashion girlie walks into a bar… She’s wearing giant bug-eyed sunglasses worthy of a praying mantis Halloween costume, a knee-length red sweater with no arm holes that would put the Lorax’s thneed to shame, split-toed Mary Janes more akin to hooves than heels, and a beat-up leather purse purposefully open and overflowing with messy personal ephemera. It may sound like the start of a corny joke or a prop list swiped from the set of Zoolander, but this is no laughing matter. This year, the most-coveted styles are, to employ an overused internet turn of phrase, so funny to me. 

A lot has been said about the rise of quiet luxury (including in this very magazine). If the think pieces and trend forecasters are to be believed, everyone should be investing in Loro Piana coats, cream-colored cashmere, and trousers tailored to the heavens. But the data says otherwise. Fashion search engine Lyst’s Q3 index points to playfully subversive brands like Miu Miu and Loewe as fashion forerunners, naming the former the hottest brand of the moment. 

For the first time in its 30-year history, Miuccia Prada’s youthful diffusion line has risen to the very top of the industry in terms of cultural relevancy. After popularizing the cheeky “no pants” trend and creating the world’s most divisive pair of sequined underwear, the brand trolled us all with a lovably strange spring runway show that featured everything from bandaids-as-accessory and bro-y boat shoes to Gigi Hadid in a pair of swim trunks. It’s a collection that makes you wonder, Is Miuccia Prada dragging me, and if so, why do I enjoy it so much?

Lyst’s list of It items also includes not one but two “ugly” shoes, a purse that looks like a sleeping bag, and a provocative “pierced” mule courtesy of Tory Burch. In reality, there’s nothing silent about fashion right now. In fact, if this season had a voice, it would sound more like a full-bodied laugh—or at least, an amused chuckle—than a hushed whisper.

The trend towards humor in fashion first started online in the murky, slow return to normalcy that followed the lockdowns of 2020. If you read the first viral fashion items of the decade like tarot cards, a clear message emerges: Irony is very much in. 

Take Internet-favorite brand Praying. The line popped off in 2021 thanks to deliciously unhinged designs that ranged from a hat declaring its wearer “God’s Favorite” to a half-joking, half-earnest fashion homage to Twilight that sold out even after several restocks. Puppets & Puppets, a line created in 2018 by art insider Carly Mark, saw its first big hit by embracing the surreal. The brand’s $545 black leather handbag, featuring a hyperreal chocolate chip cookie accent in lieu of a logo, was a breakout TikTok star in 2022. On its face, the cookie purse is a bizarre choice for an everyday handbag, but if you are willing to laugh at yourself, the saccharine design is surprisingly suitable for any occasion because of its versatile color palette. 

The humble boat tote also got an ironic fashion makeover in the summer of 2022. Previously a hallmark of those who use summer as a verb and sensible beachgoers, L.L. Bean’s preppy staple became an unexpected It item as Instagram creators embroidered their bags with pithy internet phrases like “unhinged” and “cry baby,” rather than the expected (and deeply unfunny) monogram.

Industry darlings, too, found success with a playful approach in 2023. Colin Locascio created the most talked-about Oscars after-party dress by putting some fanciful flowers on comedy royalty Iris Apatow. Christian Cowan’s giant puffball dress wreaked havoc on a traditionally staid Paris Fashion Week when she crashed into Sam Smith in the front row. And, of course, Marc Jacobs’s strange little passion project, Heaven, now rivals its sister lines in terms of hype and engagement. Between its weirdo designs (like a handcuffed shoulder bag) and viral campaigns featuring a wry combination of fresh and not-as-fresh faces, Heaven successfully embraces the wacky fringes of the fashion industry.

But it’s brands like J.W. Anderson’s Loewe that manage to make an expensive fashion joke feel worth your hard-earned cash. The most recent Loewe runway show married quality and craftsmanship with off-kilter silhouettes for instant archival classics. I dare you not to crack a smile at their comically high-waisted (but no less beautifully made) trousers. Just try to not laugh (or cry) at the ultimate cozy red sweater, full-length and, tragically, cut without arms. And please, contain yourself around the pat-of-butter evening dress. She’s likely to melt under pressure. 

Last but certainly not least, Schiaparelli’s surrealist sensibility has ushered in a whole new era of red-carpet fashion, dressing Natasha Leon and Kylie Jenner in Dali-esque, gold-dripping creations. Whether he’s designing literal ear jewelry (and I’m not talking about earrings) or a giant velvet champagne cape (because why not?), much like the house’s namesake, Daniel Roseberry loves to confuse and delight. His Midas touch basically guarantees viral success on the red carpet, and even if you’re not a fan of, say, lion heads as evening wear or a life-size gold lobster necklace, you can’t help but respect someone who is—at least they’ve got a sense of humor about things. 

A good laugh can be a winning formula for selling luxury, too. Canadian online retailer Ssense recently emerged as everyone’s favorite fashion Instagram account thanks to their witty captions and self-aware fashion in-jokes. (I, too, identify as a Clean Girl moon, Feral Girl rising, Girlboss sun.) And that’s by design. “Ultimately, luxury fashion is a business of emotions—and the most relatable human emotion is humor,” explains Steff Yotka, Head of Digital Content at Ssense, about the brand’s unique approach to sh*tposting. “It’s also the hardest emotion to telegraph correctly, especially online, which is why I think a lot of designers and brands, perhaps, avoid it.” That said, Yotka stresses that there’s nothing new about comedy in fashion — brands like Thom Browne, Jean Paul Gaultier, and Vivienne Westwood have been here for years — but she loves that clothing with a “little sense of mischief” is thriving now. 

It’s not difficult to understand the appeal — cookie bags especially. After all, who among us didn’t crave a cheeky little conversation starter to dispel any lingering post-pandemic where-do-i-put-my-hands social awkwardness? Resuming office life, commuting in subway cars full of strangers, and returning to social events that you might even need to *gasp* leave your house for created a social void in the world — funny fashion helped fill it. 

In a world of TikTok nihilism, economic turmoil, and an impending climate crisis, taking your look too seriously can feel like an emotionally fatal mistake. Would you wear a carefully considered blazer to face the apocalypse? Probably not, which is why today’s most relevant fashion brands wink at the absurdity of modern life rather than running from it. They’re clothes that say, “I know I’m silly, but you deserve a hit of dopamine.” 

So, don’t believe the rumors. Fashion is louder than ever. It isn’t about exclusionary designs, high prices, or showing off (well, maybe there’s a little of that). And it’s not about wearability or shopping. It’s about emotion. The most interesting voices in the industry, the ones that really cut through the noise, delight their fans and encourage expression through personal style. Whether it’s subversive humor you crave or a silly little puffball, there’s a designer to make you laugh. You just have to listen.