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Fashion When it comes to ugly-cute fashion, is there a line?

Jan. 20, 2022
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The debate of what makes something “ugly-cute” is as old as fashion itself. Especially with the widespread revival of vintage fashion, spanning from ‘70s disco style to incredibly campy Y2K clothes entering the mainstream, the gap between what’s hideous and what’s iconic seems extremely small. 


The question here isn’t necessarily one of good taste. TikTok is a perfect microcosm of various trends straying from a one-size-fits-all approach to personal style that can be deemed cool or “current.” With the resurgence of vintage, it seems like everything goes. On and off social media, I see a punk approach to repurposing clothing of the ‘90s, a revival of hippie aesthetics of ‘70s women like Stevie Nicks and Penny Laneand Juicy Couture tracksuits and almost-sold-out low-top Ugg boots reminiscent of the Y2K era. Interestingly, none of these aesthetics center on garments being expensive, new, or maybe even cute. With the revival of vintage and sustainable practices culminating in an overhaul of many previous views on fashion, here’s the million-dollar question: why does everyone love testing the boundaries of the ugly-versus-cute binary so much? 


Maybe it’s about references. Marc Jacobs, for example, just dropped a gray shirt that simply has "The Virgin Suicides" written in cursive on the front. The Virgin Suicides references epitomize the Sofia Coppola aesthetic resonating with angsty Gen Zers. The Heaven x Coppola collab is refined, one-of-a-kind, and cool-girl-bitchy-chic à la the protagonists of The Virgin Suicides, The Bling Ring, and Marie Antoinette. So when you see someone wearing the “Virgin Suicides” baby tee to your morning lecture, or a floor-length skirt of the movie poster, it’s not just because they loved the cut of the t-shirt or the one line of embroidery on the front; it’s about signaling their appreciation of the director and movies being referenced.   


Jacobs has based his brand entirely on ‘90s references and grunge aesthetics, with plenty of cropped graphic tees hailing iconic film director Gregg Araki and featuring phrases like “more teen angst.” When it was first getting popular, Heaven was promoted heavily by Gen-Z celebrity-influencers like Sydney Sweeney, Enya Umanzor, and Devon Carlson. Heaven has never just been about wearing Heaven; it’s about wearing whatever obscure, freshly-out-of-the-vault alt-kid trend Jacobs and his team have decided to popularize. Sometimes it’s on the more glamorous end of the spectrum, inspired by someone like Sofia Coppola, and other times it’s a vinyl purse with E.T. printed on it, or kitschy teddy bear backpack charms. 


A couple weeks ago on Depop, I discovered a $40 white tank top flaunting a photo of Julius the Monkey (from the once infamous Y2K brand Paul Frank) accompanied by the text “WHO THE HELL IS THIS.” I thought it was one of the funniest things I’d ever seen; it unlocked some deep memories of the cringeworthy Paul Frank ensembles I used to wear in elementary school. Then, when I thought about it more, I became genuinely fascinated. It made me wonder—what got us to this tank top, culturally and cosmically? The tank top is the epitome of our current ugly-cute fashion moment, because it’s all about nostalgia. Articles of clothing like the Paul Frank top unlock core memories of when we were all coming into our own. No one is going to argue that the monkey print of Paul Frank is actually gorgeous—but no one cares, either. It’s a perfect example of nostalgia’s best, what with its reference to a Y2K high camp aesthetic and its hilarious tone. 


Amidst the return of Y2K aesthetics, Uggs might be the most viral example of a product toeing the line between cute and campy. The brand’s revival even has its own TikTok audio. You can’t spend five minutes on TikTok or any Gen-Z celebrity’s Instagram without encountering the Ugg slipper—specifically the short (or “ultra micro”) Ugg iteration Vogue has written about. Vogue cites Emily Ratajkowski, Kendall Jenner, and Joan Smalls as the supermodel seals of approval for wearing a “shrunken, shorter, way more universally flattering, sleeker, and more discreet” version of the Uggs popularized by the most Y2K of Y2K stars—think Nicole Richie and Paris Hilton. 


Gen Z seems acutely aware of the slippery slope between ugly and iconic. The result is outfits that are equal parts funny, whimsical, and cool in what they’re referencing. I’ve been seeing TikTokers (see: Caroline Ricke) donning Ashley Tisdale-era dresses-over-jeans looks. I never thought the day would come, partly because as soon as I realized how awful my style was at 15, I vowed to forget about my mid-2010s fashion faux pas as much as humanly possible. But maybe rejecting modernity and embracing Y2K kitsch tradition is a way to accept our cringiest, freest adolescent selves. Are dresses over jeans cute? No. Is the look cool? Maybe. Is it in and getting thousands of TikTok likes? Absolutely. The cringey 2000s were the best of times, they were the worst of times! 


Every time I see low-rise jeans, tiny purses, or Paul Frank tanks, I’m immediately reminded of the films, celebrities, trends, and stores of my childhood. What matters to me is that when I recently found my hot pink Uggs and black velour Juicy Couture tracksuit, I screamed with joy. I also recently bought micro brown Uggs, and saw an executive at my internship wearing the same shoes around the office. So if I want to wear an outfit that makes me feel like I just watched Gwen Stefani’s “Hollaback Girl” music video for the first time, I feel like 2022 is definitely giving me the thumbs-up to do so. My point is, wearing ugly-cute clothes is fun—and that experience isn’t contingent on whether a clothing item can be classically defined as fashionable or refined.