If you’re anything like me, then The Princess Diaries’ “ugly” high schooler to beautiful princess makeover scene probably resulted in decades of frying your hair pin-straight, overplucking your brows, and throwing your tiny, wired glasses directly into the bin. By now, we’ve seen similar transformations plenty of times in films: the awkward, nerdy girl at school undergoes a life-changing glow-up – ultimately “revealing” that the character was actually beautiful the entire time [shocking!] and securing her a brand new, it-girl status among the popular girls and high school bullies. In most cases, the before-and-afters particularly fixated on trading in everything “ugly” about the characters – frizzy hair, geeky glasses, bushy brows, and frumpy clothes – for pretty, sleek, and skin-baring options.  

Today, however, hot people everywhere seem to be reversing the plot – filling our Instagram feeds with the opposite of stereotypical “hot” dressing. In short: librarian glasses, frumpy grandma cardigans, pooling jorts, long-hanging rat tails, ultra-layered sportswear, low-slung maxi skirts, and skin-tight capris [aka all the trends you once probably thought you’d retired for good] are undeniably in. For proof, just scroll through Instagram’s latest generation of fashion models and it-girls to catch Gabbriette and Bella Hadid peeking out from behind a pair of tiny rectangular glasses, Iris Law accessorising puffy sports shorts with two long, dangling hair strands falling from her bob, or Emma Chamberlain tucking a bunched-up Maison Margiela bodysuit into a pair of fishnet tights. 

So… when did all the fashion girls start disguising themselves as ugly ducklings? We explored the hottest, and most surprising trend of 2023’s origins below.

Hear us out: with cute labels like Kitten, Simone Rocha, and 16Arlington in the mix, plus Miu Miu’s viral underwear-as-trousers looks for SS24 [see below], we won’t be leaving naked dressing behind anytime soon. It does, however, seem that ugly dressing first arose as a contrast to the late 2010s’ ultra skin-baring fashion trends. Remember when Kim Kardashian wore a barely-there water droplet dress to the Met Ball in 2019? Or Rihanna’s iconic glistening, sheer dress and nude thong in 2014 and Miley Cyrus’ stripped-down “Wrecking Ball” music video look way back in 2010? Well, in the year of our lord 2023, the fashion crowd is layering-up pleated mini-skirts over jeans, pointy kitten heels over chunky men’s socks, and windbreakers over jumpers over polos topped with kitschy trucker hats. Could it be that TikTok users’ forecasts of “recession-core” – a predicted wave of scaled-back or modest fashion in response to 2023’s looming recession – are finally coming true via ugly it-girl looks? With the “ugly” trend’s more-is-more layering and chaotic, piled-on accessories, we can’t be entirely sure.

If we do know one thing, however, it’s that we don’t make the rules, Mrs. P does. And frankly, what Miuccia says, goes – especially when it comes to what the biggest models are wearing. In fact – besides Prada’s long-standing history of turning out ugly-meets-sexy designs – it’s quirky younger sister label Miu Miu first signalled the trend at its SS22 show, which saw a procession of models walk the runway in dowdy trousers, blue school boy shirts, low-slung librarian skirts, and sensible jumpers. Since then, Miu Miu has presented a masterclass of ugly-chic style, all culminating with this past season’s collection which showcased clunky, clear glasses, drawstring swim trunks, and flat, braided sandals accessorised with neon toe-plasters among a cast of dishevelled, greasy-haired girls for SS24. ICYMI, it was Miuccia who once said “ugly is attractive, ugly is exciting,” alleging that true fashion comes from rewriting beauty standards and cliches as we know them – turns out, Gen Z’s it-girls have been taking note.

Of all the ways that ugly dressing has filtered into the fashion crowd, one of the most prolific by far is via TikTok’s viral “How to dress like you’re from the Lower East Side” trend. If you’ve spent any time on the app over the last few weeks, you’ve probably heard the fun, instructional sound playing in the background as users try out the uniform favoured by the neighbourhood’s Gen Z residents. “First you need a maxi skirt – make it really ugly,” a voice narrates on the viral sound, while girls pile on the clothing items listed: baby tees from the children’s section, loafers or cowboy boots, wispy braided hair, gas-station sunglasses, a DIY-style hobo bag, silver jewellery, and big, clunky headphones. While we’re sure that coquettish Lower East Side dressing didn’t prompt hot girls to start cosplaying as ugly, it does embody the trend’s mash-up of viral Y2K microtrends – from the wrap-around sunnies to chunky shoes, low-waisted maxi skirts, and XXL jorts. “High fashion slay!” one user commented on Emma Chamberlain’s Margiela bodysuit look, admiring the messy aesthetic created by her awkward amalgamation of items. Sure, disguising yourself as ugly in the name of fashion might not be for everyone, but – as with other niche online trends – it’s certainly being embraced by the internet.