Ugg boots, low-rise jeans, and ballet pumps—I’ve watched these Y2K trends make a comeback with mixed feelings. Every time a new 2000s style returns, I think, “Please, just not shorts and tights!”
In the late 2000s, during Gordon Brown’s time as Prime Minister, layering tiny shorts over black tights was the ultimate trend—at least for young, fashion-loving women who splurged at Topshop. Alexa Chung styled them with chic collared blouses, Sienna Miller paired them with boho tops, and the Gossip Girl cast flaunted them on the Upper East Side, often swapping black for bold, colorful tights.
No one questioned the discomfort of polyester rubbing under denim—or worse, another synthetic fabric. No one mentioned the risk of looking more like a pantomime extra than a chic Parisian. But as the new decade arrived, the trend thankfully faded. Aside from rare Chanel runway sightings, it disappeared, joining other fashion missteps of the era, buried in grainy old Facebook photos.
“The interesting thing is that many embracing Y2K fashion were either babies or not even born during that era,” says Riani Kenyon, anthropologist and behavioral analyst at Canvas8. If I didn’t already feel old, I certainly do now. Kenyon calls this trend “fauxstalgia”—a romanticized version of the past, shaped by cultural references and curated aesthetics.
Bella Hadid, a driving force behind the Y2K fashion comeback, recently stepped out in glossy, low-denier tights under black hotpants at her brand launch. Suki Waterhouse was spotted in frayed denim cut-offs, tights, and a massive fur coat—so 2009 that I had to double-check the date. On Instagram, influencers are styling Molly-Mae-inspired beige blazers with shorts and sheer tights. Even Alexa Chung, the original shorts-and-tights trendsetter, is bringing back the look she made famous nearly 20 years ago.
This trend originally emerged as a practical compromise. In the late 2000s, denim hotpants were the ultimate style statement—just think of Kate Moss at Glastonbury in hers with Hunter wellies. But for those in colder climates, bare legs weren’t exactly ideal—unless you fancied flirting with hypothermia. Layering cut-offs over tights offered a thin, snag-prone shield against the cold while keeping the same “cool” silhouette. Plus, pairing shorts with hosiery made them feel a little less, well, short.
In theory, this was the perfect transitional look—ideal for a cool summer day or a warm autumn afternoon. In reality, it never quite made sense. You were either too sweaty or freezing. At a British festival, you could experience all of the above in one day. Wellies and tights, especially in damp weather, were a disaster waiting to happen—I’m still amazed I avoided trench foot at Leeds Festival 2009.
Despite all this, super-short shorts over 60-denier tights became a go-to outfit formula. And it wasn’t just about denim. Kate Moss’s first Topshop collection featured a striped yellow pair—practically unwearable unless toned down with tights. Going for the now-iconic “indie sleaze” vibe? House of Holland’s Pretty Polly collab had you covered with bold, cartoonish tights—think oversized polka dots, stars, and faux suspender prints.
For a breezier, boho look, I had some floaty floral shorts from Urban Outfitters, which I paired with my least laddered tights. I told myself that, while I might not look as cool as Florence (whom I’d seen, soggy-footed, at Leeds), I could at least pass for a lost member of her Machine. I later found out my siblings had been secretly calling those shorts “the pantaloons.”
Perhaps the worst version of the trend was the “business casual” look. When I was studying for my A-Levels, the shorts-tights combo was at its peak. At my sixth form, we were required to wear “office” attire to supposedly prep us for the corporate world. It already felt outdated, a relic of the Eighties. Now, friends who’ve become successful lawyers dress far more casually for work than we ever did lounging in the common room. Naturally, we got creative, pairing “city shorts” with black opaques.
When do shorts become “city shorts,” you ask? When they’re essentially office trousers chopped off at the knee. My classmates wore them in grey, beige, and greige, often with pinstripes or checks. The more fashion-forward versions tapered slightly at the knee, giving the wearer the look of an aristocrat on a golfing weekend—especially if paired with, dare I say it, a waistcoat (another inexplicable Noughties trend making a comeback). We were aiming for executive chic, but we ended up looking like we were about to join Toad of Toad Hall on a wild adventure.
